Herbicidal sulfonamides

ABSTRACT

Sulfonamides such as N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1,3-dihydro-6-methyl-3-oxofuro[3,4-c]pyridine-4-sulfonamide are useful as herbicides and plant growth regulants.

RELATED APPLICATION

This application is a continuation-in-part of application U.S. Ser. No. 732,091, filed May 9, 1985, now abandoned.

BACKGROUND OF THE INVENTION

Herbicidal sulfonamides such as N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1,3-dihydro-6-methyl-3-oxofuro[3,4-c]pyridine-4-sulfonamide are useful as agricultural chemicals and, in particular, as herbicides and growth regulants.

European Publication No. 13,480 (published July 23, 1980) discloses herbicidal pyridine-2-, -3- and -4-sulfonylureas.

U.S. Pat. No. 4,456,469 issued 6/29/84 discloses herbicidal pyridine-3-sulfonylureas of the formula ##STR1## wherein R is C₁ -C₆ alkyl, C₃ -C₆ alkenyl, C₂ -C₄ alkoxyalkyl or C₅ -C₆ cycloalkyl; and ##STR2##

U.S. Pat. No. 4,465,506 issued 8/14/84 discloses herbicidal sulfonylureas of Formula I, II and III ##STR3## wherein ##STR4## R is, inter alia, H, Cl, Br, NO₂, C₁ -C₃ alkyl; ##STR5## R₈ is H, CH₃ or Cl; R₉ is H or CH₃ ; and

R₁₀ is H or CH₃.

U.S. Pat. No. 4,369,320 issued 1/18/83 discloses herbicidal quinoline sulfonylureas of the formula ##STR6## wherein ##STR7## W is O or S; and R₁ is, inter alia, H, Cl, F, Br, OCH₃, CH₃, or NO₂.

EP-A-79,683 discloses herbicidal sulfonylureas, including those of general Formulae IV and V: ##STR8## wherein Q is O, S or SO₂ ;

R₂ is H or C₁ -C₃ alkyl;

R₃ is H or CH₃ ; and

R₄ is H or CH₃.

EP-A-107,979 discloses herbicidal sulfonylureas of formula ##STR9## wherein J is, among other values, ##STR10## A is a heterocyclic pyrimidine, triazine, triazole or a derivative thereof.

South African Patent Application No. 83/5165 (Swiss priority 7/16/82, published 1/16/84) discloses herbicidal sulfonamides of the formula ##STR11## wherein A is an unsubstituted or substituted bridge of 3 or 4 atoms which contains 1 or 2 oxygen, sulfur or nitrogen atoms and, together with the linking carbon atom, forms a non-aromatic 5- or 6-membered heterocyclic ring system, with the proviso that two oxygen atoms are separated by at least one carbon atom and that oxygen and sulfur atoms are only linked to each other if the sulfur atom takes the form of the --SO-- or SO₂ -- group.

South African Patent Application No. 84/3522 (Swiss priority 5/11/83, published 11/11/84) discloses herbicidal sulfonamides of formula ##STR12## wherein A is an unsubstituted or substituted unsaturated bridge of 4 atoms, of the formula --CH═CH--Y--, wherein Y is a bridge member of 2 atoms which is selected from the series consisting of --NH--CO--, --NH--SO₂ --, --S--CO--, --S--SO₂ --, --O--CO-- or --O--SO₂ --.

The need still exists, however, for general and selective herbicides.

SUMMARY OF THE INVENTION

This invention relates to novel compounds of Formula I, suitable agricultural compositions containing them and their method-of-use as general preemergence and/or postemergence herbicides or plant growth regulants. ##STR13## wherein ##STR14## E is a bridge of 3 or 4 atoms, which may be substituted or unsubstituted, containing 0-2 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen, and also containing 1-4 atoms of carbon, said bridge together with two carbon attachment sites forming a partially saturated 5- or 6-membered carbocyclic or heterocyclic ring; or E is a bridge of 3 or 4 atoms, which may be substituted or unsubstituted, containing 0-1 heteroatoms selected from oxygen or sulfur, 0-2 heteroatoms of nitrogen and 1-4 atoms of carbon, said bridge together with two carbon attachment sites forming a fully unsaturated 5- or 6-membered carbocyclic or heterocyclic ring, with the proviso that when E contains two atoms of oxygen or sulfur, they must be separated by at least one atom of carbon, and that oxygen and sulfur are only linked to each other if the sulfur is in the form of SO or SO₂ ; in the bridging group E, sulfur may take the form of S, SO or SO₂, and one of the atoms of carbon may be a carbonyl, thiocarbonyl or the cyclic 5- and 6-membered ketals thereof; when one of the bridging atoms is a substituted carbon, the substituent on said carbon includes H, halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₃ -C₄ alkenyl, C₃ -C₄ haloalkenyl, C₃ -C₄ alkynyl, C₃ -C₄ haloalkynyl, C₁ -C₃ alkoxycarbonyl, CN, NO₂, OH, C₁ -C₃ alkoxy, C₁ -C₃ haloalkoxy, C₁ -C₃ alkylthio, C₁ -C₃ alkylsulfinyl, C₁ -C₃ alkylsulfonyl, C₁ -C₃ alkylcarbonyl, C₁ -C₃ alkylsulfamoyl, di(C₁ -C₃ alkyl)sulfamoyl and C₁ -C₂ alkyl substituted with C₁ -C₂ alkoxy, C₁ -C₂ alkylthio or CN; when the bridging atom is nitrogen (other than nitrogen in the form of a cyclic sulfonamide), substituents on said nitrogen include H, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₃ -C₄ alkenyl, C₃ -C₄ haloalkenyl, C₃ -C₄ alkynyl, C₃ -C₄ haloalkynyl, C₁ -C₃ alkoxy, C₁ -C₄ alkylcarbonyl, C₁ -C₃ alkoxycarbonyl, C₁ -C₃ alkylaminocarbonyl or C₁ -C₄ alkylsulfonyl; when the bridging atom is nitrogen in the form of a cyclic sulfonamide, then the nitrogen is substituted by R₆ as defined below;

W is O or S;

R is H or CH₃ ;

n is 0 or 1;

R₁ is H, CH₃, OCH₃ or Cl;

R₂ is H, C₁ -C₃ alkyl, Cl, Br, F, C₁ -C₃ alkoxy, C₁ -C₃ alkylthio, CF₃, CH₂ OCH₃, CH₂ SCH₃ or CH₂ CN;

R₃ is H, C₁ -C₃ alkyl, halogen, C₁ -C₃ alkoxy, C₁ -C₃ alkylthio, C₁ -C₂ alkylsulfonyl, C₁ -C₂ alkylcarbonyl, C₁ -C₂ alkoxycarbonyl, C₃ -C₄ alkenyl, NO₂, NH₂, C₁ -C₂ alkylamino, di(C₁ -C₂)alkylamino, C₁ -C₂ alkylsulfamoyl, di(C₁ -C₂)alkylsulfamoyl, (C₁ -C₂ alkyl)aminocarbonyl, di(C₁ -C₂ alkyl)aminocarbonyl or C₃ -C₄ alkynyl;

R₆ is H, R₈ ', SR₈ ', SO₂ R₈, OR₈ ', C(O)R₈, L, C(O)L, CO₂ R₈ ', (CO)₂ OR₈ ', (CO)₂ R₈ ', C(O)NR₉ R₁₀, C(O)NRA, C(S)SR₈ ', NH₂, NR₉ R₁₀, OH, CN, P(O)R₁₁ R₁₂, P(S)R₁₁ R₁₂ or Si(CH₃)₂ R₁₃ ;

R₈ is C₁ -C₁₀ alkyl, C₃ -C₁₀ alkoxyalkoxyalkyl, C₂ -C₁₀ alkenyl, C₃ -C₁₀ epoxyalkyl, C₂ -C₁₀ alkynyl, C₃ -C₆ cycloalkyl, C₄ -C₇ cycloalkylalkyl or phenyl optionally substituted with R₁₄ ;

when R₈ is C₃ -C₆ cycloalkyl or C₄ -C₇ cycloalkylalkyl, it may optionally be substituted by C₁ -C₄ alkyl, 1 to 3 atoms of Cl or F or 1 Br; when R₈ is C₁ -C₁₀ alkyl, C₂ -C₁₀ alkenyl or C₂ -C₁₀ alkynyl, it may optionally be substituted by one or more halogens and/or by (R₁₅)_(r) provided that when r is 2, the values of R₁₅ may be identical or different;

R₈ ' is C₁ -C₁₀ alkyl, C₃ -C₁₀ alkoxyalkoxyalkyl, C₃ -C₁₀ alkenyl, C₃ -C₁₀ epoxyalkyl, C₃ -C₁₀ alkynyl, C₃ -C₆ cycloalkyl, C₄ -C₇ cycloalkylalkyl or phenyl optionally substituted with R₁₄ ; when R₈ ' is C₃ -C₆ cycloalkyl or C₄ -C₇ cycloalkylalkyl, it may optionally be substituted by C₁ -C₄ alkyl, 1 to 3 atoms of Cl or F or 1 Br; when R₈ ' is C₁ -C₁₀ alkyl, C₃ -C₁₀ alkenyl or C₃ -C₁₀ alkynyl, it may optionally be substituted by one or more halogens and/or by (R₁₅)_(r) provided that when r is 2, the values of R₁₅ may be identical or different;

r is 0, 1 or 2:

R₉ is H or C₁ -C₄ alkyl;

R₁₀ is H, C₁ -C₁₀ alkyl, C₁ -C₁₀ haloalkyl, C₃ -C₁₀ alkenyl, C₃ -C₁₀ alkynyl, C₃ -C₆ cycloalkyl or phenyl substituted with R₁₄ ;

R₁₀ ' is C₁ -C₁₀ alkyl, C₁ -C₁₀ haloalkyl, C₃ -C₁₀ alkenyl, C₃ -C₁₀ alkynyl, C₃ -C₆ cycloalkyl or phenyl substituted with R₁₄ ;

R₁₁ and R₁₂ are independently C₁ -C₄ alkyl, C₁ -C₄ alkoxy or C₁ -C₄ alkylthio;

R₁₃ is C₁ -C₁₀ alkyl, benzyl or phenyl optionally substituted with R₁₄ ;

R₁₄ is H, F, Cl, Br, CH₃, OCH₃, NO₂, CN, SCH₃, SO₂ CH₃ or CF₃ ;

R₁₅ is OR₁₀, OC(O)R₁₀, OC(O)NR₉ R₁₀, OSO₂ R₁₀ ', OP(O)R₁₁ R₁₂, OSi(CH₃)₂ R₁₃, SR₁₀, SOR₁₀ ', SO₂ R₁₀ ', SCN, CN, SP(O)R₁₁ R₁₂, SP(S)R₁₁ R₁₂, P(O)R₁₁ R₁₂, P(S)R₁₁ R₁₂, NR₉ R₁₀, N+R₉ R₁₀ R₁₃, NR₉ C(O)R₁₀, NR₉ C(O)OR₁₀ ', NR₉ C(O)NR₉ R₁₀, NR₉ SO₂ R₁₀ ', NR₉ P(O)R₁₁ R₁₂, NR₉ P(S)R₁₁ R₁₂, NO₂, C(O)R₁₀, C(O)OR₁₀, C(O)NR₉ R₁₀, C(R₁₀)═NOR₁₂, naphthyl, L, phenyl optionally substituted with R₁₄ and/or R₁₆, ##STR15## R₁₆ is H, F, Cl or Br; L is a 5- or 6-membered aromatic heterocyclic, a 5- or 6-membered dihydroaromatic heterocycle or a 5- or 6-membered tetrahydroaromatic heterocycle which contains 1-4 heteroatoms selected from 0-1 oxygen atoms, 0-1 sulfur atoms and/or 0-4 nitrogen atoms and these heterocycles may optionally be substituted by 1-4 CH₃, 1-2 OCH₃, SCH₃, Cl, N(CH₃)₂ or CN groups or L is a 5- or 6-membered lactone, lactam or cycloalkanone which may optionally be substituted by 1-4 CH₃ groups; ##STR16## X is H, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, C₁ -C₄ haloalkyl, C₁ -C₄ haloalkylthio, C₁ -C₄ alkylthio, halogen, C₂ -C₅ alkoxyalkoxy, amino, C₁ -C₃ alkylamino or di(C₁ -C₃ alkyl)amino;

Y is H, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, C₁ -C₄ haloalkylthio, C₁ -C₄ alkylthio, C₂ -C₅ alkoxyalkyl, C₂ -C₅ alkoxyalkoxy, amino, C₁ -C₃ alkylamino, di(C₁ -C₃ alkyl)amino, C₃ -C₄ alkenyloxy, C₃ -C₄ alkynyloxy, C₂ -C₅ alkylsulfinylalkyl, C₁ -C₄ haloalkyl, C₂ -C₅ alkylsulfonylalkyl, C₃ -C₅ cycloalkyl, C₂ -C₄ alkynyl, C₂ -C₅ alkylthioalkyl, ##STR17## or N(OCH₃)CH₃ ; W₁ and W₂ are independently O or S;

m is 2 or 3;

R_(a) is H or CH₃ ;

R_(b) is C₁ -C₂ alkyl;

R_(c) is C₁ -C₂ alkyl;

Z is CH, N, CCH₃, CC₂ H₅, CCl or CBr;

Y₁ is O or CH₂ ;

X₁ is CH₃, OCH₃, OC₂ H₅ or OCF₂ H;

X₂ is CH₃, C₂ H₅ or CH₂ CF₃ ;

Y₂ is OCH₃, OC₂ H₅, SCH₃, SC₂ H₅, OCF₂ H, SCF₂ H, CH₃ or CH₂ CH₃ ;

X₃ is CH₃ or OCH₃ ;

Y₃ is H or CH₃ ;

X₄ is CH₃, OCH₃, OC₂ H₅, CH₂ OCH₃ or Cl;

Y₄ is CH₃, OCH₃, OC₂ H₅ or Cl; and

Z₁ is CH or N;

and their agriculturally suitable salts; provided that

(a) when W is S, then R is H, A is A-1, Z is CH or N, and Y is CH₃, OCH₃, OC₂ H₅, CH₂ OCH₃, C₂ H₅, CF₃, SCH₃, OCH₂ CH═CH₂, OCH₂ C.tbd.CH, OCH₂ CH₂ OCH₃, CH(OCH₃)₂ or ##STR18## (b) when X is Cl, Br, F or I, then Z is CH and Y is OCH₃, OC₂ H₅, NH₂, NHCH₃, N(CH₃)₂ or OCF₂ H;

(c) when X or Y is C₁ haloalkoxy, then Z is CH;

(d) in compounds of Formula Ia, either R₁ or R₂ must be H;

(e) when the total number of carbon atoms in X and Y is greater than 4, then the total number of carbon atoms in R₁, R₂, R₃ and the bridging group E is less than or equal to 10;

(f) X₄ and Y₄ are not simultaneously Cl;

(g) the total number of carbon atoms in R₆ is less than or equal to 12; and

(h) when R₁₅ and the bridging nitrogen of a cyclic sulfonamide are attached to the same carbon then R₁₅ is other than OH, SH, OC(O)R₁₀, OC(O)NR₉ R₁₀, OSO₂ R₁₀ ', OP(O)R₁₁ R₁₂, OSi(CH₃)₂ R₁₃, SP(O)R₁₁ R₁₂, SP(S)R₁₁ R₁₂, NR₉ R₁₀ or N+R₉ R₁₀ R₁₃.

In the above definitions, the term "alkyl", used either alone or in compound words such as "alkylthio" or "haloalkyl", denotes straight chain or branched alkyl, e.g. methyl, ethyl, n-propyl, 2-propyl or the different butyl, pentyl, hexyl, heptyl, octyl, nonyl or decyl isomers.

Alkoxy denotes methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butyl, pentyl, hexyl, heptyl, octyl or nonyl isomers.

Alkenyl denotes straight chain or branched alkenes, e.g. vinyl, 1-propenyl, 2-propenyl, isopropenyl and the different butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl or decenyl isomers.

Alkynyl denotes straight chain or branch alkynes, e.g., ethynyl, 1-propynyl, 2-propynyl and the different butynyl, pentynyl, hexynyl, heptynyl, octynyl, nonynyl and decynyl isomers.

Alkylcarbonyl denotes, e.g., acetyl and propionyl.

Alkoxycarbonyl denotes, e.g., methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl and isopropoxycarbonyl.

Alkylsulfonyl denotes methylsulfonyl, ethylsulfonyl and the different propylsulfonyl isomers.

Alkylthio, alkylsulfinyl, alkylamino, alkylsulfamoyl, etc. are defined analogously to the above examples.

Cycloalkyl denotes cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

The term "halogen", either alone or in compound words such as "haloalkyl", denotes fluorine, chlorine, bromine or iodine.

The total number of carbon atoms in a substituent group is indicated by the C_(i) -C_(j) prefix where i and j are numbers from 1 to 10. For example, C₂ -C₅ alkylsulfonylalkyl would designate CH₂ SO₂ CH₃ through (CH₂)₄ SO₂ CH₃ or CH₂ SO₂ C₄ H₉, C₂ alkoxyalkoxy would designate OCH₂ OCH₃, C₂ cyanoalkyl would designate CH₂ CN and C₃ cyanoalkyl would designate CH₂ CH₂ CN and CH(CN)CH₃.

It would be recognized by one skilled in the art that when R₁₅ is OH or SH, that these substituents cannot be bonded to the same carbon as another heteroatom or to an olefinic or acetylenic carbon atom.

Preferred for reasons of greater ease of synthesis and/or greater herbicidal efficacy are:

1. Compounds of Formula I where J is Ia.

2. Compounds of Preferred 1 where J is ##STR19## q is 0 or 1; Q is O, S, or NR₄ ;

Q₁ is O, S, SO, SO₂, NH or NCH₃ ;

Q₂ is O, S, NH, NCH₃, CH₂ or CHCH₃ ;

Q₃ is O, S, NH, NCH₃ or CH₂ ;

R₄ is H or C₁ -C₄ alkyl;

R₅ is H or CH₃ ;

R₇ is H or C₁ -C₃ alkyl;

R₁₇ is H or C₁ -C₄ alkyl;

R₁₈ is H or CH₃ ;

R₁₉ is H, F, Cl or C₁ -C₄ alkyl;

R₂₀ is H, F, Cl or CH₃ ;

R₂₁ is H, C₁ -C₃ alkyl, C₁ -C₃ alkoxy, F or Cl;

R₂₂ is H, CH₃, C₁ -C₃ alkoxy, F, Cl or OH; or

R₂₁ and R₂₂ can be taken together to form --OCH₂ CH₂ O-- or --OCH₂ CH₂ CH₂ O--;

R₂₃ is H, C₁ -C₃ alkyl, C₁ -C₃ alkoxy, Cl, Br or F; provided that

(a) the total number of carbon atoms in R₁₉ and R₂₀ is less than or equal to 4;

(b) the total number of carbon atoms in R₄ and R₅ is less than or equal to 4;

(c) when R₂₁ is C₁ -C₃ alkoxy, then R₂₂ is H, CH₃ or C₁ -C₃ alkoxy; and

(d) when R₂₂ is OH, then R₂₁ is H or C₁ -C₃ alkyl, and when R₂₂ is C₁ -C₃ alkoxy, then R₂₁ is H, C₁ -C₃ alkyl or C₁ -C₃ alkoxy.

3. Compounds of Preferred 2 where

n is 0;

W is O;

R is H;

X is CH₃, OCH₃, OC₂ H₅, Cl, Br, F, I, OCF₂ H, CH₂ F, CF₃, OCH₂ CH₂ F, OCH₂ CHF₂, OCH₂ CF₃, CH₂ Cl or CH₂ Br;

Y is H, CH₃, OCH₃, OC₂ H₅, CH₂ OCH₃, NHCH₃, N(OCH₃)CH₃, N(CH₃)₂, CH₂ CH₃, CF₃, SCH₃, OCH₂ CH═CH₂, OCH₂ C.tbd.CH, CH₂ OCH₂ CH₃, OCH₂ CH₂ OCH₃, CH₂ SCH₃, CH₂ SCH₂ CH₃, ##STR20## OCF₂ H, SCF₂ H, CH.tbd.CH or C.tbd.CCH₃ ; and Z is CH or N.

4. Compounds of Preferred 3 where

R₂ is H, CH₃, OCH₃, Cl or Br;

R₆ is H, R₈ ', C(O)R₈ or CO₂ R₈ ';

R₈ and R₈ ' are C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, C₃ -C₆ alkenyl, C₃ -C₆ haloalkenyl, C₃ -C₆ alkynyl, C₃ -C₆ epoxyalkyl or C₁ -C₄ alkyl substituted with C₁ -C₂ alkoxy, C₁ -C₂ alkylthio, C₁ -C₂ alkylsulfinyl, C₁ -C₂ alkylsulfonyl, CO₂ (C₁ -C₂ alkyl, C(O)C₁ -C₂ alkyl, CN or OH;

R₁₉ is H or C₁ -C₃ alkyl;

R₂₀ is H or CH₃ ;

R₂₁ is H, C₁ -C₃ alkyl or C₁ -C₂ alkoxy;

R₂₂ is H, CH₃, C₁ -C₂ alkoxy or OH; or

R₂₁ and R₂₂ may be taken together to form --OCH₂ CH₂ O-- or --OCH₂ CH₂ CH₂ O--; and

R₂₃ is H, CH₃, Cl, Br or OCH₃.

5. Compounds of Preferred 4 where R₈ and R₈ ' are C₁ -C₆ alkyl, C₁ -C₄ haloalkyl, C₃ -C₄ alkenyl, C₃ -C₄ haloalkenyl, C₃ -C₄ alkynyl, CO₂ (C₁ -C₂ alkyl), C(O)C₁ -C₂ alkyl or C₁ -C₃ alkyl substituted with C₁ -C₂ alkoxy, C₁ -C₂ alkylthio, C₁ -C₂ alkylsulfonyl or CN.

6. Compounds of Preferred 5 where

A is A-1;

X is CH₃, OCH₃, OC₂ H₅, Cl, OCF₂ H or OCH₂ CF₃ ; and

Y is CH₃, OCH₃, C₂ H₅, CH₂ OCH₃, NHCH₃ or CH(OCH₃)₂.

7. Compounds of Preferred 6 where J is J₁.

8. Compounds of Preferred 6 where J is J₃.

9. Compounds of Preferred 6 where J is J₅.

10. Compounds of Preferred 6 where J is J₇.

11. Compounds of Preferred 6 where J is J₉.

12. Compounds of Preferred 6 where J is J₁₁.

13. Compounds of Preferred 6 where J is J₁₃.

14. Compounds of Preferred 6 where J is J₁₅.

15. Compounds of Preferred 6 where J is J₁₇.

16. Compounds of Preferred 6 where J is J₁₉.

17. Compounds of Preferred 6 where J is J₂₁.

18. Compounds of Preferred 6 where J is J₂₃.

19. Compounds of Preferred 6 where J is J₂₆.

20. Compounds of Preferred 6 where J is J₂₈.

21. Compounds of Formula I where J is Ib.

22. Compounds of Preferred 21 where J is ##STR21## q is 0 or 1; Q is O, S, or NR₄ ;

Q₁ is O, S, SO, SO₂, NH or NCH₃ ;

Q₂ is O, S, NH, NCH₃, CH₂ or CHCH₃ ;

Q₃ is O, S, NH, NCH₃ or CH₂ ;

R₄ is H or C₁ -C₄ alkyl;

R₅ is H or CH₃ ;

R₇ is H or C₁ -C₃ alkyl;

R₁₇ is H or C₁ -C₄ alkyl;

R₁₈ is H or CH₃ ;

R₁₉ is H, F, Cl or C₁ -C₄ alkyl;

R₂₀ is H, F, Cl or CH₃ ;

R₂₁ is H, C₁ -C₃ alkyl, C₁ -C₃ alkoxy, F or Cl;

R₂₂ is H, CH₃, C₁ -C₃ alkoxy, F, Cl or OH; or

R₂₁ and R₂₂ can be taken together to form --OCH₂ CH₂ O-- or --OCH₂ CH₂ CH₂ O--;

R₂₃ is H, C₁ -C₃ alkyl, C₁ -C₃ alkoxy, Cl, Br or F; provided that

(a) the total number of carbon atoms in R₁₉ and R₂₀ is less than or equal to 4;

(b) the total number of carbon atoms in R₄ and R₅ is less than or equal to 4;

(c) when R₂₁ is C₁ -C₃ alkoxy, then R₂₂ is H, CH₃ or C₁ -C₃ alkoxy; and

(d) when R₂₂ is OH, then R₂₁ is H or C₁ -C₃ alkyl, and when R₂₂ is C₁ -C₃ alkoxy, then R₂₁ is H, C₁ -C₃ alkyl or C₁ -C₃ alkoxy.

23. Compounds of Preferred 22 where

n is 0;

W is O;

R is H;

X is CH₃, OCH₃, OC₂ H₅, Cl, Br, F, I, OCF₂ H, CH₂ F, CF₃, OCH₂ CH₂ F, OCH₂ CHF₂, OCH₂ CF₃, CH₂ Cl or CH₂ Br;

Y is H, CH₃, OCH₃, OC₂ H₅, CH₂ OCH₃, NHCH₃, N(OCH₃)CH₃, N(CH₃)₂, CH₂ CH₃, CF₃, SCH₃, OCH₂ CH═CH₂, OCH₂ C.tbd.CH, CH₂ OCH₂ CH₃, OCH₂ CH₂ OCH₃, CH₂ SCH₃, CH₂ SCH₂ CH₃, ##STR22## OCF₂ H, SCF₂ H, CH.tbd.CH or C.tbd.CCH₃ ; and Z is CH or N.

24. Compounds of Preferred 23 where

R₂ is H, CH₃, OCH₃, Cl or Br;

R₃ is CH₃, CH₂ CH₃, F, Cl, Br, OCH₃, OCH₂ CH₃, SCH₃ SCH₂ CH₃, SO₂ CH₃, SO₂ CH₂ CH₃, SO₂ N(CH₃)₂, C(O)NHCH₃ or C(O)N(CH₃)₂ ;

R₆ is H, R₈ ', C(O)R₈ or CO₂ R₈ ';

R₈ and R₈ ' are C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, C₃ -C₆ alkenyl, C₃ -C₆ haloalkenyl, C₃ -C₆ alkynyl, C₃ -C₆ epoxyalkyl or C₁ -C₄ alkyl substituted with C₁ -C₂ alkoxy, C₁ -C₂ alkylthio, C₁ -C₂ alkylsulfinyl, C₁ -C₂ alkylsulfonyl, CO₂ (C₁ -C₂ alkyl), C(O)C₁ -C₂ alkyl, CN or OH;

R₁₉ is H or C₁ -C₃ alkyl;

R₂₀ is H or CH₃ ;

R₂₁ is H, C₁ -C₃ alkyl or C₁ -C₂ alkoxy;

R₂₂ is H, CH₃, C₁ -C₂ alkoxy or OH; or

R₂₁ and R₂₂ may be taken together to form --OCH₂ CH₂ O-- or --OCH₂ CH₂ CH₂ O--; and

R₂₃ is H, CH₃, Cl, Br or OCH₃.

25. Compounds of Preferred 24 where

R₈ and R₈ ' are C₁ -C₆ alkyl, C₁ -C₄ haloalkyl, C₃ -C₄ alkenyl, C₃ -C₄ haloalkenyl, C₃ -C₄ alkynyl, CO₂ (C₁ -C₂ alkyl), C(O)C₁ -C₂ alkyl or C₁ -C₃ alkyl substituted with C₁ -C₂ alkoxy, C₁ -C₂ alkylthio, C₁ -C₂ alkylsulfonyl or CN.

26. Compounds of Preferred 25 where

A is A-1;

X is CH₃, OCH₃, OC₂ H₅, Cl, OCF₂ H or OCH₂ CF₃ ; and

Y is CH₃, OCH₃, C₂ H₅, CH₂ OCH₃, NHCH₃ or CH(OCH₃)₂.

27. Compounds of Preferred 26 where J is J₂.

28. Compounds of Preferred 26 where J is J₄.

29. Compounds of Preferred 26 where J is J₆.

30. Compounds of Preferred 26 where J is J₈.

31. Compounds of Preferred 26 where J is J₁₀.

32. Compounds of Preferred 26 where J is J₁₂.

33. Compounds of Preferred 26 where J is J₁₄.

34. Compounds of Preferred 26 where J is J₁₆.

35. Compounds of Preferred 26 where J is J₁₈.

36. Compounds of Preferred 26 where J is J₂₀.

37. Compounds of Preferred 26 where J is J₂₂.

38. Compounds of Preferred 26 where J is J₂₄.

39. Compounds of Preferred 26 where J is J₂₇.

40. Compounds of Preferred 26 where J is J₂₉.

41. Compounds of Formula I where J is Ic.

42. Compounds of Preferred 41 where J is ##STR23## and R₂₃ is H, C₁ -C₃ alkyl, C₁ -C₃ alkoxy, Cl, Br or F.

43. Compounds of Preferred 42 where

W is O;

R is H;

X is CH₃, OCH₃, OC₂ H₅, Cl, Br, F, I, OCF₂ H, CH₂ F, CF₃, OCH₂ CH₂ F, OCH₂ CHF₂, OCH₂ CF₃, CH₂ Cl or CH₂ Br;

Y is H, CH₃, OCH₃, OC₂ H₅, CH₂ OCH₃, NHCH₃, N(OCH₃)CH₃, N(CH₃)₂, CH₂ CH₃, CF₃, SCH₃, OCH₂ CH═CH₂, OCH₂ C.tbd.CH, CH₂ OCH₂ CH₃, OCH₂ CH₂ OCH₃, CH₂ SCH₃, CH₂ SCH₂ CH₃, ##STR24## OCF₂ H, SCF₂ H, CH.tbd.CH or C.tbd.CCH₃ ; and Z is CH or N.

44. Compounds of Preferred 43 where R₂ is H, CH₃, OCH₃, Cl or Br; R₃ is H, CH₃, CH₂ CH₃, F, Cl, Br, OCH₃, OCH₂ CH₃, SCH₃, SCH₂ CH₃, SO₂ CH₃, SO₂ CH₂ CH₃, SO₂ N(CH₃)₂, C(O)NHCH₃ or C(O)N(CH₃)₂ ; and R₂₃ is H, CH₃, Cl, Br or OCH₃.

45. Compounds of Preferred 44 where

A is A-1;

X is CH₃, OCH₃, OC₂ H₅, Cl, OCF₂ H or OCH₂ CF₃ ; and

Y is CH₃, OCH₃, C₂ H₅, CH₂ OCH₃, NHCH₃ or CH(OCH₃)₂.

Specifically preferred for reasons of their highest herbicidal activity, greatest plant growth regulant activity and/or most favorable ease of synthesis are;

N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]thieno[2,3-c]pyridine-7-sulfonamide, m.p. 183°-186° C.(d); and

N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]thieno2,3-c]pyridine-7-sulfonamide, m.p. 182°-184° C.(d).

DETAILED DESCRIPTION OF THE INVENTION Synthesis

The preparation of N-oxides, such as Ia (n=1) and Ib (n=1), from the corresponding pyridines, such as Ia (n=0) and Ib (n=0) can be carried out by any of several known methods as described in Chemistry of the Heterocyclic N-Oxides, Katritzky and Lagowski, Academic Press, New York, 1971.

The compounds of Formula I can be prepared by one or more of the methods described below in Equations 1, 2, 3 and 4.

As shown in Equation 1, compounds of Formula I, where J is other than J₉ and J₁₀, can be prepared by reacting a sulfonylisocyanate (W=0) or a sulfonylisothiocyanate (W=S) of Formula II with an appropriate heterocyclic amine of Formula III, wherein R and A are as previously defined.

Equation 1 ##STR25##

The reaction is carried out at 25° to 100° C. in an inert, aprotic solvent such as methylene chloride or xylene for 0.5 to 24 hours as taught in U.S. Pat. No. 4,127,405.

Compounds of Formula I, where W is S and R is H, (Id) can be prepared by reacting the appropriate sulfonamide of Formula IV with a heterocyclic isothiocyanate of Formula V, as shown in Equation 2.

Equation 2 ##STR26##

The reaction is carried out at 25° to 80° C. in an inert, aprotic solvent such as acetone or acetonitrile in the presence of a base such as potassium carbonate for 0.5 to 24 hours. The required heterocyclic isothiocyanates V are prepared from the corresponding amines III as taught in EPO Publication No. 35,893.

Compounds of Formula I, where W is O (Ie) and J is other than J₁, J₂, J₅, J₆, J₁₇, J₁₈, J₂₆, J₂₇, J₂₈, and J₂₉ can be prepared by reacting the sulfonamides of Formula IV with an appropriate methylcarbamate of Formula VI in the presence of an equimolar amount of trimethylaluminum, as shown in Equation 3.

Equation 3 ##STR27##

The reaction is carried out at 25° to 40° in a solvent such as methylene chloride for 10 to 96 hours under an inert atmosphere as taught in EPO Publication No. 84,244 (7/27/83). The required carbamates VI are prepared by reacting the corresponding amines III with dimethylcarbonate or methyl chloroformate in the presence of a strong base.

Alternatively, compounds of Formula Ie can be prepared by reacting a sulfonylcarbamate of Formula VII with an appropriate amine of Formula III, as shown in Equation 4.

Equation 4 ##STR28##

The reaction is carried out at 50° to 100° C. in a solvent such as dioxane for 0.5 to 24 hours as taught in U.S. Pat. No. 4,443,243. The required carbamates VII are prepared by reacting the corresponding sulfonamides IV with diphenylcarbonate in the presence of a strong base.

The intermediate sulfonylisocyanates (W=O) and sulfonylisothiocyanates (W=S) of Formula II from Equation 1 can be prepared as shown in Equations 5, 6 and 7.

As shown in Equation 5, sulfonylisocyanates of Formula IIa, where J is other than J₉ and J₁₀, can be prepared by the reaction of sulfonamides of Formula IV with phosgene in the presence of n-butylisocyanate and a tertiary amine catalyst, at reflux in a solvent such as xylene by the method of U.S. Pat. No. 4,238,621.

Equation 5 ##STR29##

The sulfonylisocyanates can also be prepared from the sulfonamides by a two step procedure involving: (a) reacting the sulfonamides with n-butylisocyanate in the presence of a base such as K₂ CO₃ at reflux in an inert solvent such as 2-butanone forming a n-butylsulfonylurea; and (b) reacting this compound with phosgene and a tertiary amine catalyst at reflux in xylene solvent. The method is similar to a procedure taught by Ulrich and Sayigh, Newer Methods of Preparative Organic Chemistry, Vol. VI, p. 223-241, Academic Press, New York and London, W. Foerst Ed.

Alternatively, as shown in Equation 6, the sulfonylisocyanates of Formula IIa can be prepared by reacting the corresponding sulfonyl chlorides VIII with cyanic acid salts.

Equation 6 ##STR30##

The reaction is carried out at 25° to 100° C. in an inert aprotic solvent such as acetonitrile for 0.5 to 24 hours in the presence of phosphorus pentoxide and an alkali metal salt such as lithium iodide according to the teachings of Japanese Pat. No. 76/26,816 (Chem. Abst., 85: 77892e (1976)).

The sulfonylisothiocyanates of Formula IIb, where J is other than J₉ and J₁₀, can be prepared as shown in Equation 7, by contacting the sulfonamides of Formula IV with carbon disulfide in the presence of two equivalents of a strong base. The resulting salt is then reacted with phosgene according to the teachings of K. Hartke, Arch. Pharm., 299, 174 (1966).

Equation 7 ##STR31##

The sulfonamides of Formula IV of Equations 2, 3, 5 and 7 are important intermediates for the preparation of the compounds of this invention. The syntheses of the required sulfonamide intermediates are described in Equations 8, 9 and 10.

As shown in Equation 8, sulfonamides of Formula IV can be prepared from the corresponding sulfonyl chlorides of Formula VIII by treatment with either anhydrous or aqueous ammonia.

Equation 8 ##STR32##

The preparation of sulfonamides from sulfonyl chlorides is widely reported in the literature; for reviews see: F. Hawking and J. S. Lawrence, "The Sulfonamides," H. K. Lewis and Co., London, 1950 and E. H. Northey, "The Sulfonamides and Allied Compounds," Reinhold Publishing Corp. New York, 1948.

The sulfonamides of Formula IV can also be prepared from the corresponding thiol IX by the three step sequence shown in Equation 9.

Equation 9 ##STR33##

The first step involves chlorination of a mercaptan such as IX to give a sulfenyl chloride, the chlorine of which is subsequently displaced in a second step with a suitable ammonia equivalent such as aqueous ammonium hydroxide to provide a sulfenamide. In a final step, the intermediate sulfenamide can be oxidized to a sulfonamide, such as IV, using an oxidizing agent such as potassium permanganate according to the methods taught by R. Lejeune, J. Pharm. Belg., 39, 217 (1984).

The unsaturated sulfonamides of Formula IVa can also be prepared from the corresponding saturated sulfonamides of Formula IVb by the two step procedure shown in Equation 10, wherein G is --SO₂ NR₆ --, --CO₂ --, --Q₂ -- or --Q₃ --, R₂₄ is R₅ or R₇, and R₂₅ is H or t-butyl.

Equation 10 ##STR34## where T₁ is CH and T₂ is N or

T₁ is N and T₂ is CH.

The first step involves benzylic bromination with N-bromosuccinimide to give a monobromide, which is subsequently dehydrobrominated in a second step by reaction with a suitable base such as triethylamine or potassium-t-butoxide in an inert solvent such as THF. This method has been used to prepare isocoumarins from 3,4-dihydroisocoumarins; see R. Barry, Chem. Rev., 64, 229 (1964).

The sulfonyl chlorides of Formula VIII of Equations 6 and 8 can be prepared from the corresponding amines X by the method shown in Equation 11.

Equation 11 ##STR35##

The reaction involves diazotization of the amine X with sodium nitrite in HCl, followed by reaction of the diazonium salt with sulfur dioxide and cupric chloride in acetic acid in analogy to the teachings of Yale and Sowinski, J. Org. Chem., 25, 1824 (1960).

Alternatively, sulfonyl chlorides of Formula VIII can be prepared by a modification of the above procedure whereby the diazotization reaction is carried out in dilute sulfuric acid and the resulting diazonium salt is reacted with sulfur dioxide, HCl and cupric chloride in a cosolvent mixture consisting of acetic acid-water (1:1) and an immiscible, inert solvent such as 1-chlorobutane or methylene chloride at 0°-40° C. for 1 to 24 hours.

Some of the sulfonyl chlorides of Formula VIII may be prepared by direct chlorosulfonation, depending on the substitution pattern on the ring and the nature of the substituent as will be known to one skilled in the art.

The sulfonyl chlorides of Formula VIII can also be prepared from the chloro compounds XI by the two step sequence shown in Equation 12.

Equation 12 ##STR36## R₂₆ =C₁ -C₄ alkyl, CH₂ C₆ H₅, or H; R₂₇ =C₁ -C₄ alkyl, CH₂ C₆ H₅, H, or C(═NH)NH₂.HCl;

M=K or Na.

The first step involves nucleophilic displacement of the chlorine atom with an alkyl or benzyl mercaptan or with thiourea to give an intermediate sulfide or thiouronium salt. The reaction can be carried out at 25° to 80° C. in a polar solvent such as DMF for 0.5 to 2 hours. The sulfide, thiol or thiouronium salt is then oxidatively chlorinated to the desired sulfonyl chloride VIII in the presence of water at -30° to 0° in an aliphatic carboxylic acid solvent such as propionic acid or a concentrated acid such as hydrochloric acid or an inert organic solvent such as dichloromethane for 1 to 24 hours. The preparation of pyridine sulfonyl chlorides, such as VIII, from mercaptans is similar to that taught by Y. Morisawa, et al., J. Med. Chem., 1980, 23, 1376-1380.

Many of the mercaptans of Formula IX in Equation 9 can be prepared from the pyridones of Formula XII as shown in Equation 13.

Equation 13 ##STR37## where G₁ is --NH--CH═CH-- or --CH═CH--NH--; and

E is as previously defined.

The thiones of Formula XIII can be prepared from the corresponding pyridones XII using base-solubilized phosphorous pentasulfide in solvents such as acetonitrile, pyridine, or dichloromethane as taught by B. Dash, et al., Heterocycles, 19, 2093 (1982) and F. Eloy and A. Deryckere, Bull. Soc. Chim. Belges, 79, 407 (1970).

Many other mercaptans can be prepared via the Newman-Karnes rearrangement of O-aryl thiocarbamates and hydrolysis of the resulting S-aryl thiocarbamates, such as XV, a representative example of which is shown in Equation 14.

The S-aryl thiocarbamates, such as XV, can also be converted directly to sulfonyl chlorides VIII via oxidative chlorination as described in Equation 12b.

Equation 14 ##STR38##

The synthesis of lactone XIV is described by W. Korytnyk and H. Ahrens, J. Med. Chem., 1971, 14, 947-952. The preparation of O-aryl thiocarbamates, their thermal rearrangement and hydrolysis is taught by M. S. Newman and H. A. Karnes, J. Org. Chem., 31, 3980 (1966), references cited therein and B. Blank, et al., J. Med. Chem., 17, 1065 (1974). The preparation of sulfonyl chlorides via the oxidative chlorination of S-aryl thiocarbamates is described by A. Wagenaar and T. Engberts, Recl. Trav. Chim. 101, 91 (1982).

Chlorides of Formula XI in Equation 12 can be obtained from pyridones XII as shown below.

Equation 15 ##STR39##

The pyridones XII can be converted to chlorides XI in the presence of phosphorous oxychloride and phosphorous pentachloride. This procedure has been used to prepare 4-chloro-1,3-dihydro-6-methyl-3-oxofuro[3,4-c]pyridine; see: W. F. Bruce and H. W. Coover, J. Am. Chem. Soc., 66, 2092 (1944). For additional examples, see: Rivalle, et al., J. Heterocyclic Chem., 13, 89-92 (1976); Bisagni, et al., ibid., 12, 461-465 (1975); Eloy and Deryckere, Bull. Soc. Chim. Belges, 79, 407-414 (1970) and Bisagni, Tetrahedron, 26, 2087 (1970).

Many other chlorides XIa can be prepared by direct chlorination of the corresponding pyridines XVI as shown in Equation 16.

Equation 16 ##STR40## where R₁, R₃ and E are as previously defined; and

E is not readily chlorinated.

The pyridines of Formula XVI are chlorinated with an appropriate chlorine source, such as sulfuryl chloride or chlorine in an aliphatic carboxylic acid solvent such as acetic acid or in an inert organic solvent such as dichloromethane for 1 to 24 hours to provide chlorides such as XIa.

The preparation of annelated pyridines such as XI, IX and X can also be carried out by any of several methods described in Pyridine and its Derivatives, G. Newkome, ed., Wiley and Sons, New York, 1984, pp. 253-445, or modifications thereof.

Many pyridones of Formula XIIb can be prepared by the condensation of a 1,3-dicarbonyl compound such as XVII and 2-cyanoacetamide as shown in Equation 17.

Equation 17 ##STR41##

The substituted 1,3-dicarbonyl compounds, prepared by methods known to one skilled in the art, are combined with 2-cyanoacetamide in a solvent such as ethanol with an appropriate base catalyst to produce pyridones such as XIIa. Acid hydrolysis and cyclization gives the desired lactone pyridone XIIb. This method is taught by S. A. Harris, et al., J. Am. Chem. Soc., 61, 1242 (1939).

Several pyridones of Formula XIIc or chlorides of Formula XIb can be obtained from pyridines such as XVIII as shown in Equation 18.

Equation 18 ##STR42## where T₃ -T₄ is N--CH or CH--N; ##STR43## where T₃ -T₄ is CH--N; ##STR44## where T₃ -T₄ is N--CH; R₄, R₅ and q are as previously defined.

An appropriately substituted diisopropylamide XVIII is combined with two equivalents of lithium diisopropylamide to give an anion according to the teachings of J. Epsztajn, Tet. Lett., 24, 4735-4738 (1983). The anion can then be trapped with a ketone, ester or epoxide at -78° to 25° C. to produce, upon workup, the alcohol XIX. The anion can also be trapped with N,N-dimethylformamide to give aldehyde XX, which on reduction also provides alcohol XIX (q=O, R₄ =R₅ =H).

Acid hydrolysis of the 2-chloro isomer XIXa provides pyridones such as XIIc. Acid hydrolysis of the 3-chloropyridines XIXb provides chlorides such as XIb.

Several other pyridones such as XIId and XIIe are more easily prepared by forming the pyridone on an existing heterocycle, examples of which are shown in Equations 19a and 19b.

Equation 19a ##STR45## where R₂₈ =H

R₂₉ = ##STR46##

Isocyanates such as XXIIa are formed in situ and cyclized to pyridones XIId as taught by F. Eloy and A. Deryckere, Bull. Soc., Chim. Belges, 79 (1970) 301-312. This method has also been used to prepare the thieno[3,2-c]pyridone isomer starting from XXIa (R₂₈ =CH═CHC(═O)N₃, R₂₉ =H).

Equation 19b ##STR47## where R₇ is as previously defined; and

R₃₀ is t-butyl.

Metallation of amides XXIIb, prepared from the corresponding acid XXIb by methods known to one skilled in the art, with 2.0 equivalents of n-butyllithium followed by quenching with N,N-dimethylformamide and para-toluenesulfonic acid afforded pyridones XIIe which may also be converted to chlorides of Formula XI by the methods described in Equation 15.

Equation 19c ##STR48##

Pyridones of Formula XIIf can be prepared following the procedures of E. Bisagni, et al., J. Heterocycl. Chem., 12, 461 (1975) as shown in Equation 19c. Treatment of pyrone XXIc with ammonium hydroxide provided the corresponding pyrone XXIIc which was alkylated with chloroacetaldehyde followed by acid work-up to afford pyridones XIIf.

The amines of Formula X, in Equation 11, can be prepared by reduction of the corresponding nitro compounds of Formula XXIII, as shown in Equation 20.

Equation 20 ##STR49##

The reduction of nitro compounds, prepared by methods known to one skilled in the art, to amines can be carried out by any of several methods as described in Preparative Organic Chemistry, 4th Ed., pp. 557-563, John Wiley and Sons, New York and London, G. Hilgetag and A. Martine, ed.; and S. A. Harris, et al., J. Am. Chem. Soc., 61, 1242 (1939).

Nitro compounds of Formula XXIIIa can be prepared by nitration of the corresponding pyridones XXIV as shown below.

Equation 21 ##STR50## where E and R₃ are as previously defined.

The nitration is carried out in strong acid, such as acetic acid, according to the method taught by Eloy and Deryckere, Bull. Soc. Chim. Belges, 79 (1970) 407-414. Pyridones XXIIIa can be converted to the corresponding pyridine chlorides as described in Equation 15.

Additional methods to prepare heterocyclic nitro compounds similar to XXIII are described in European Publication No. 107,979.

The synthesis of heterocyclic amines such as those represented by Formula III has been reviewed in "The Chemistry of Heterocyclic Compounds," a series published by Interscience Publ., New York and London. Aminopyrimidines are described by D. J. Brown in "The Pyrimidines," Vol. XVI of the series mentioned above, which is herein incorporated by reference. The 2-amino-1,3,5-triazines of Formula III, where A is A-1 and Z is N, can be prepared according to methods described by E. M. Smolin and L. Rapaport in "s-Triazines and Derivatives," Vol. XIII.

Pyrimidines of Formula III, where A is A-1 and Y is an acetal or thioacetal substituent, can be prepared by methods taught in European Publication No. 84,244 (published July 27, 1983).

Pyrimidines of Formula III, where A is A-1 and Y is cyclopropyl or OCF₂ H, can be synthesized according to the methods taught in South African Patent Application No. 83/7434 and South African Publication No. 82/5045, respectively.

Compounds of Formula III, where A is A-2 or A-3, can be prepared by procedures disclosed in U.S. Pat. No. 4,339,267.

Compounds of Formula III, where A is A-5, can be prepared by methods taught in U.S. Pat. No. 4,421,550.

Compounds of Formula III, where A is A-6, can be prepared by methods taught in European Publication No. 94,260 (published Nov. 16, 1983).

The preparation of the compounds of this invention is further illustrated by the following examples.

EXAMPLE 1 1,3-Dihydro-6-methyl-oxofuro[3,4-c]pyridine-4-thiouronium salt

A solution of 6.0 g of 4-chloro-1,3-dihydro-6-methyl-oxofuro[3,4-c]pyridine [prepared using the procedure of W. F. Bruce and H. W. Coover, J. Am. Chem. Soc., 66, 2092 (1944)] and 2.5 g of thiourea in 25 mL DMF was heated at 50° to 60° C. for 3 hours. After cooling, the resulting precipitate was collected by filtration and washed with ether to provide 6.74 g of the title compound as a yellow solid, m.p. 205°-208° C.(d).

EXAMPLE 2 4-(Hydroxymethyl)-2-mercapto-6-methyl-3-pyridinecarboxylic acid

A solution of 6 g of the above thiouronium salt was dissolved in 10% sodium hydroxide. After 15 minutes the solution was acidified with 10% HCl. The resulting precipitate was collected by filtration and washed with water to provide the title compound as a yellow solid, m.p. >270° C.

EXAMPLE 3 1,3-Dihydro-6-methyl-3-oxofuro[3,4-c]pyridine-4-sulfonamide

A mixture of 2.0 g of the compound from Example 2, 17 mL of water, 33 mL of methylene chloride and 2.1 mL of concentrated HCl was cooled to -5° C. Keeping the temperature between 5° and 10° C., 35 mL of a 6% sodium hypochlorite solution was added over 15 minutes. After an additional 20 minutes at 0° C., the mixture was poured into water and extracted with methylene chloride. The organic phase was washed with sodium bisulfite and dried over sodium sulfate.

The solution of the sulfonyl chloride was cooled to -78° C. and 5 mL of dry ammonia added dropwise. After slowly warming to room temperature, the mixture was acidified with 10% HCl to pH 2 and sodium chloride added to give a saturated solution. The mixture was extracted with ethyl acetate to obtain 0.25 g of the title compound as a solid, m.p. 211°-213° C.

EXAMPLE 4 N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-1,3-dihydro-6-methyl-3-oxofuro[3,4-c]pyridine-4-sulfonamide

To a suspension of 0.21 g of the compound from Example 3 and 0.25 g of N-(4,6-dimethoxypyrimidin-2-yl)phenyl carbamate in 2 mL acetonitrile is added 0.14 mL 1,8-diazabicyclo[5.4.0]undec-7-ene. After 15 minutes, 6 mL water is added, followed by dropwise addition of 10% HCl. The resulting precipitate is collected by filtration and washed with water to provide 0.09 g of the title compound, m.p. 149°-153° C.

Using the procedures of Equations 1-21 and Examples 1-4, the following compounds of Tables 1-13 can be made by one skilled in the art. Where relevant, n=0 unless otherwise noted.

                                      TABLE 1                                      __________________________________________________________________________      ##STR51##                                                                     J q Q   R.sub.1                                                                            R.sub.2                                                                            R.sub.3                                                                            R.sub.4                                                                           R.sub.5                                                                            X   Y   m.p. (°C.)                           __________________________________________________________________________     J.sub.1                                                                          0 O   H   H   --  H  H   CH.sub.3                                                                           CH.sub.3                                        J.sub.1                                                                          0 O   H   H   --  H  H   CH.sub.3                                                                           OCH.sub.3                                       J.sub.1                                                                          0 O   H   H   --  H  H   OCH.sub.3                                                                          OCH.sub.3                                       J.sub.1                                                                          0 O   H   H   --  H  H   Cl  OCH.sub.3                                       J.sub.1                                                                          0 O   H   H   --  H  CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                        J.sub.1                                                                          0 O   H   CH.sub.3                                                                           --  CH.sub.3                                                                          CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                       J.sub.1                                                                          0 O   H   CH.sub.3                                                                           --  H  H   CH.sub.3                                                                           CH.sub.3                                        J.sub.1                                                                          0 O   H   CH.sub.3                                                                           --  H  H   CH.sub.3                                                                           OCH.sub.3                                       J.sub.1                                                                          0 O   H   CH.sub.3                                                                           --  H  H   OCH.sub.3                                                                          OCH.sub.3                                                                          149-153                                     J.sub.1                                                                          0 O   H   CH.sub.3                                                                           --  H  H   Cl  OCH.sub.3                                       J.sub.1                                                                          0 O   H   Cl  --  H  H   OCH.sub.3                                                                          OCH.sub.3                                       J.sub.1                                                                          0 O   H   OCH.sub.3                                                                          --  H  H   Cl  OCH.sub.3                                       J.sub.1                                                                          0 O   Cl  H   --  H  H   CH.sub.3                                                                           CH.sub.3                                        J.sub.1                                                                          0 O   CH.sub.3                                                                           H   --  H  H   CH.sub.3                                                                           OCH.sub.3                                       J.sub.1                                                                          0 S   H   H   --  H  H   CH.sub.3                                                                           OCH.sub.3                                       J.sub.1                                                                          0 NH  H   H   --  H  H   OCH.sub.3                                                                          OCH.sub.3                                       J.sub.1                                                                          0 NCH.sub.3                                                                          H   H   --  H  H   CH.sub.3                                                                           OCH.sub.3                                       J.sub.1                                                                          1 O   H   H   --  H  H   CH.sub.3                                                                           CH.sub.3                                        J.sub.1                                                                          1 O   H   H   --  H  H   CH.sub.3                                                                           OCH.sub.3                                       J.sub.1                                                                          1 O   H   H   --  H  H   OCH.sub.3                                                                          OCH.sub.3                                       J.sub.1                                                                          1 O   H   H   --  H  H   Cl  OCH.sub.3                                       J.sub.1                                                                          1 O   H   H   --  H  CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                        J.sub.1                                                                          1 O   H   H   --  H  CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                       J.sub.1                                                                          1 O   H   H   --  H  CH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                       J.sub.1                                                                          1 O   H   H   --  H  CH.sub.3                                                                           Cl  OCH.sub.3                                       J.sub.1                                                                          1 O   H   H   --  CH.sub.3                                                                          CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                       J.sub.1                                                                          1 O   H   Cl  --  H  H   OCH.sub.3                                                                          OCH.sub.3                                       J.sub.1                                                                          1 O   H   OCH.sub.3                                                                          --  H  H   Cl  OCH.sub.3                                       J.sub.1                                                                          1 S   H   H   --  H  H   CH.sub.3                                                                           OCH.sub.3                                       J.sub.1                                                                          1 NH  H   H   --  H  H   OCH.sub.3                                                                          OCH.sub.3                                       J.sub.1                                                                          1 NCH.sub.3                                                                          H   H   --  H  H   Cl  OCH.sub.3                                       J.sub.2                                                                          0 O   H   --  H   H  H   CH.sub.3                                                                           OCH.sub.3                                       J.sub.2                                                                          0 O   H   --  H   H  H   OCH.sub.3                                                                          OCH.sub.3                                       J.sub.2                                                                          0 O   H   --  H   H  CH.sub.3                                                                           Cl  OCH.sub.3                                       J.sub.2                                                                          0 O   H   --  H   CH.sub.3                                                                          CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                       J.sub.2                                                                          0 O   H   --  Cl  H  H   OCH.sub.3                                                                          OCH.sub.3                                       J.sub.2                                                                          0 O   H   --  Cl  H  H   Cl  OCH.sub.3                                       J.sub.2                                                                          0 O   H   --  Cl  H  H   CH.sub.3                                                                           CH.sub.3                                        J.sub.2                                                                          0 O   H   --  OCH.sub.3                                                                          H  H   CH.sub.3                                                                           OCH.sub.3                                       J.sub.2                                                                          0 O   H   --  CH.sub.3                                                                           H  H   OCH.sub.3                                                                          OCH.sub.3                                       J.sub.2                                                                          0 O   CH.sub.3                                                                           --  H   H  H   CH.sub.3                                                                           OCH.sub.3                                       J.sub.2                                                                          0 O   Cl  --  H   H  H   OCH.sub.3                                                                          OCH.sub.3                                       J.sub.2                                                                          0 O   OCH.sub.3                                                                          --  H   H  H   Cl  OCH.sub.3                                       J.sub.2                                                                          0 O   CH.sub.3                                                                           --  CH.sub.3                                                                           H  H   CH.sub.3                                                                           OCH.sub.3                                       J.sub.2                                                                          0 O   Cl  --  Cl  H  H   OCH.sub.3                                                                          OCH.sub.3                                       J.sub.2                                                                          0 S   H   --  H   H  H   CH.sub.3                                                                           OCH.sub.3                                       J.sub.2                                                                          0 NH  H   --  H   H  H   OCH.sub.3                                                                          OCH.sub.3                                       J.sub.2                                                                          0 NCH.sub.3                                                                          H   --  H   H  H   Cl  OCH.sub.3                                       J.sub.2                                                                          1 O   H   --  H   H  H   CH.sub.3                                                                           CH.sub.3                                        J.sub.2                                                                          1 O   H   --  H   H  H   CH.sub.3                                                                           OCH.sub.3                                       J.sub. 2                                                                         1 O   H   --  H   H  H   OCH.sub.3                                                                          OCH.sub.3                                       J.sub.2                                                                          1 O   H   --  H   H  H   Cl  OCH.sub.3                                       J.sub.2                                                                          1 O   H   --  H   H  CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                       J.sub.2                                                                          1 O   H   --  H   CH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                       J.sub.2                                                                          1 O   H   --  Cl  H  H   CH.sub.3                                                                           OCH.sub.3                                       J.sub.2                                                                          1 O   H   --  CH.sub.3                                                                           H  H   OCH.sub.3                                                                          OCH.sub.3                                       J.sub.2                                                                          1 O   H   --  OCH.sub.3                                                                          H  H   Cl  OCH.sub.3                                       J.sub.2                                                                          1 O   Cl  --  H   H  H   CH.sub.3                                                                           OCH.sub.3                                       J.sub.2                                                                          1 O   CH.sub.3                                                                           --  H   H  H   OCH.sub.3                                                                          OCH.sub.3                                       J.sub.2                                                                          1 O   OCH.sub.3                                                                          --  H   H  H   Cl  OCH.sub.3                                       J.sub.2                                                                          1 O   Cl  --  Cl  H  H   CH.sub.3                                                                           OCH.sub.3                                       J.sub.2                                                                          1 O   CH.sub.3                                                                           --  CH.sub.3                                                                           H  H   OCH.sub.3                                                                          OCH.sub.3                                       J.sub.2                                                                          1 S   H   --  H   H  H   Cl  OCH.sub.3                                       J.sub.2                                                                          1 NH  H   --  H   H  H   CH.sub.3                                                                           OCH.sub.3                                       J.sub.2                                                                          1 NCH.sub.3                                                                          H   --  H   H  H   OCH.sub.3                                                                          OCH.sub.3                                       J.sub.17                                                                         --                                                                               --  H   H   --  -- H   Cl  OCH.sub.3                                       J.sub.17                                                                         --                                                                               --  H   H   --  -- H   CH.sub.3                                                                           OCH.sub.3                                       J.sub.17                                                                         --                                                                               --  H   H   --  -- CH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                       J.sub.17                                                                         --                                                                               --  H   Cl  --  -- H   CH.sub.3                                                                           OCH.sub.3                                       J.sub.17                                                                         --                                                                               --  Cl  H   --  -- H   OCH.sub.3                                                                          OCH.sub.3                                       J.sub.18                                                                         --                                                                               --  H   --  H   -- H   Cl  OCH.sub.3                                       J.sub.18                                                                         --                                                                               --  H   --  H   -- H   CH.sub.3                                                                           OCH.sub.3                                       J.sub.18                                                                         --                                                                               --  H   --  H   -- CH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                       J.sub.18                                                                         --                                                                               --  Cl  --  Cl  -- H   Cl  OCH.sub.3                                       __________________________________________________________________________

                                      TABLE 1a                                     __________________________________________________________________________      ##STR52##                                                                     J q Q   R.sub.1                                                                            R.sub.2                                                                            R.sub.3                                                                            R.sub.4                                                                           R.sub.5                                                                           X    Y    m.p. (°C.)                          __________________________________________________________________________     J.sub.1                                                                          0 O   H   H   --  H  H  CH.sub.3                                                                            CH.sub.3                                        J.sub.1                                                                          0 O   H   H   --  H  H  CH.sub.3                                                                            OCH.sub.3                                       J.sub.1                                                                          0 O   H   H   --  H  H  OCH.sub.3                                                                           OCH.sub.3                                       J.sub.1                                                                          0 O   H   H   --  H  H  NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                               J.sub.1                                                                          0 O   H   H   --  H  CH.sub.3                                                                          CH.sub.3                                                                            CH.sub.3                                        J.sub.1                                                                          0 O   H   CH.sub.3                                                                           --  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            OCH.sub.3                                       J.sub.1                                                                          0 O   H   CH.sub.3                                                                           --  H  H  CH.sub.3                                                                            CH.sub.3                                        J.sub.1                                                                          0 O   H   CH.sub.3                                                                           --  H  H  CH.sub.3                                                                            OCH.sub.3                                       J.sub.1                                                                          0 O   H   CH.sub.3                                                                           --  H  H  OCH.sub.3                                                                           OCH.sub.3                                       J.sub.1                                                                          0 O   H   CH.sub.3                                                                           --  H  H  NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                               J.sub.1                                                                          0 O   H   Cl  --  H  H  OCH.sub.3                                                                           OCH.sub.3                                       J.sub.1                                                                          0 O   H   OCH.sub.3                                                                          --  H  H  NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                               J.sub.1                                                                          0 O   Cl  H   --  H  H  CH.sub.3                                                                            CH.sub.3                                        J.sub.1                                                                          0 O   CH.sub.3                                                                           H   --  H  H  CH.sub.3                                                                            OCH.sub.3                                       J.sub.1                                                                          0 S   H   H   --  H  H  CH.sub.3                                                                            OCH.sub.3                                       J.sub.1                                                                          0 NH  H   H   --  H  H  OCH.sub.3                                                                           OCH.sub.3                                       J.sub.1                                                                          0 NCH.sub.3                                                                          H   H   --  H  H  CH.sub.3                                                                            OCH.sub.3                                       J.sub.1                                                                          1 O   H   H   --  H  H  CH.sub.3                                                                            CH.sub.3                                        J.sub.1                                                                          1 O   H   H   --  H  H  CH.sub.3                                                                            OCH.sub.3                                       J.sub.1                                                                          1 O   H   H   --  H  H  OCH.sub.3                                                                           OCH.sub.3                                       J.sub.1                                                                          1 O   H   H   --  H  H  NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                               J.sub.1                                                                          1 O   H   H   --  H  CH.sub.3                                                                          CH.sub.3                                                                            CH.sub.3                                        J.sub.1                                                                          1 O   H   H   --  H  CH.sub.3                                                                          CH.sub.3                                                                            OCH.sub.3                                       J.sub.1                                                                          1 O   H   H   --  H  CH.sub.3                                                                          OCH.sub.3                                                                           OCH.sub.3                                       J.sub.1                                                                          1 O   H   H   --  H  CH.sub.3                                                                          NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                               J.sub.1                                                                          1 O   H   H   --  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            OCH.sub.3                                       J.sub.1                                                                          1 O   H   Cl  --  H  H  OCH.sub.3                                                                           OCH.sub.3                                       J.sub.1                                                                          1 O   H   Cl  --  H  H  OCH.sub.3                                                                           OCH.sub.3                                       J.sub.1                                                                          1 O   H   OCH.sub.3                                                                          --  H  H  NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                               J.sub.1                                                                          1 S   H   H   --  H  H  CH.sub.3                                                                            OCH.sub.3                                       J.sub.1                                                                          1 NH  H   H   --  H  H  OCH.sub.3                                                                           OCH.sub.3                                       J.sub.1                                                                          1 NCH.sub.3                                                                          H   H   --  H  H  NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                               J.sub.2                                                                          0 O   H   --  H   H  H  CH.sub.3                                                                            OCH.sub.3                                       J.sub.2                                                                          0 O   H   --  H   H  H  OCH.sub.3                                                                           OCH.sub.3                                       J.sub.2                                                                          0 O   H   --  H   H  CH.sub.3                                                                          NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                               J.sub.2                                                                          0 O   H   --  H   CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            OCH.sub.3                                       J.sub.2                                                                          0 O   H   --  Cl  H  H  OCH.sub.3                                                                           OCH.sub.3                                       J.sub.2                                                                          0 O   H   --  Cl  H  H  NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                               J.sub.2                                                                          0 O   H   --  Cl  H  H  CH.sub.3                                                                            CH.sub.3                                        J.sub.2                                                                          0 O   H   --  OCH.sub.3                                                                          H  H  CH.sub.3                                                                            OCH.sub.3                                       J.sub.2                                                                          0 O   H   --  CH.sub.3                                                                           H  H  OCH.sub.3                                                                           OCH.sub.3                                       J.sub.2                                                                          0 O   CH.sub.3                                                                           --  H   H  H  CH.sub.3                                                                            OCH.sub.3                                       J.sub.2                                                                          0 O   Cl  --  H   H  H  OCH.sub.3                                                                           OCH.sub.3                                       J.sub.2                                                                          0 O   OCH.sub.3                                                                          --  H   H  H  NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                               J.sub.2                                                                          0 O   CH.sub.3                                                                           --  CH.sub.3                                                                           H  H  CH.sub.3                                                                            OCH.sub.3                                       J.sub.2                                                                          0 O   Cl  --  Cl  H  H  OCH.sub.3                                                                           OCH.sub.3                                       J.sub.2                                                                          0 S   H   --  H   H  H  CH.sub.3                                                                            OCH.sub.3                                       J.sub.2                                                                          0 NH  H   --  H   H  H  OCH.sub.3                                                                           OCH.sub.3                                       J.sub.2                                                                          1 O   H   --  H   H  H  CH.sub.3                                                                            CH.sub.3                                        J.sub.2                                                                          1 O   H   --  H   H  H  CH.sub.3                                                                            OCH.sub.3                                       J.sub.2                                                                          1 O   H   --  H   H  H  OCH.sub.3                                                                           OCH.sub.3                                       J.sub.2                                                                          1 O   H   --  H   H  H  NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                               J.sub.2                                                                          1 O   H   --  H   H  CH.sub.3                                                                          CH.sub.3                                                                            OCH.sub.3                                       J.sub.2                                                                          1 O   H   --  H   CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           OCH.sub.3                                       J.sub.2                                                                          1 O   H   --  Cl  H  H  CH.sub.3                                                                            OCH.sub.3                                       J.sub.2                                                                          1 O   H   --  CH.sub.3                                                                           H  H  OCH.sub.3                                                                           OCH.sub.3                                       J.sub.2                                                                          1 O   H   --  OCH.sub.3                                                                          H  H  NHCH.sub.3                                                                          CH.sub.2 CH.sub.2                               J.sub.2                                                                          1 O   Cl  --  H   H  H  CH.sub.3                                                                            OCH.sub.3                                       J.sub.2                                                                          1 O   CH.sub.3                                                                           --  H   H  H  OCH.sub.3                                                                           OCH.sub.3                                       J.sub.2                                                                          1 O   OCH.sub.3                                                                          --  H   H  H  NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                               J.sub.2                                                                          1 O   Cl  --  Cl  H  H  CH.sub.3                                                                            OCH.sub. 3                                      J.sub.2                                                                          1 O   CH.sub.3                                                                           --  CH.sub.3                                                                           H  H  OCH.sub.3                                                                           OCH.sub.3                                       J.sub.2                                                                          1 S   H   --  H   H  H  NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                               J.sub.2                                                                          1 NH  H   --  H   H  H  CH.sub.3                                                                            OCH.sub.3                                       J.sub.2                                                                          1 NCH.sub.3                                                                          H   --  H   H  H  OCH.sub.3                                                                           OCH.sub.3                                       J.sub.17                                                                         --                                                                               --  H   H   --  -- H  NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                               J.sub.17                                                                         --                                                                               --  H   H   --  -- H  CH.sub.3                                                                            OCH.sub.3                                       J.sub.17                                                                         --                                                                               --  H   H   --  -- CH.sub.3                                                                          OCH.sub.3                                                                           OCH.sub.3                                       J.sub.17                                                                         --                                                                               --  H   Cl  --  -- H  CH.sub.3                                                                            OCH.sub.3                                       J.sub.17                                                                         --                                                                               --  Cl  H   --  -- H  OCH.sub.3                                                                           OCH.sub.3                                       J.sub.18                                                                         --                                                                               --  H   --  H   -- H  NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                               J.sub.18                                                                         --                                                                               --  H   --  H   -- H  CH.sub.3                                                                            OCH.sub.3                                       J.sub.18                                                                         --                                                                               --  H   --  H   -- CH.sub.3                                                                          OCH.sub.3                                                                           OCH.sub.3                                       J.sub.18                                                                         --                                                                               --  Cl  --  Cl  -- H  NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                               __________________________________________________________________________

                                      TABLE 2                                      __________________________________________________________________________      ##STR53##                                                                     J q R.sub.1                                                                            R.sub.2                                                                            R.sub.3                                                                            R.sub.4                                                                           R.sub.6 R.sub.7                                                                           X   Y   m.p. (°C.)                        __________________________________________________________________________     J.sub.3                                                                          0 H   H   --  H  H       -- CH.sub.3                                                                           CH.sub.3                                     J.sub.3                                                                          0 H   H   --  H  H       -- CH.sub.3                                                                           OCH.sub.3                                    J.sub.3                                                                          0 H   H   --  H  H       -- Cl  OCH.sub.3                                    J.sub.3                                                                          0 H   H   --  H  CH.sub.3                                                                               -- CH.sub.3                                                                           OCH.sub.3                                    J.sub.3                                                                          0 H   H   --  H  CH.sub.3                                                                               -- CH.sub.3                                                                           CH.sub.3                                     J.sub.3                                                                          0 H   H   --  H  CH.sub.3                                                                               -- OCH.sub.3                                                                          OCH.sub.3                                    J.sub.3                                                                          0 H   H   --  H  CH.sub.3                                                                               -- OCH.sub.3                                                                          OCH.sub.3                                    J.sub.3                                                                          0 H   H   --  H  CH.sub.3                                                                               -- Cl  OCH.sub.3                                    J.sub.3                                                                          0 H   H   --  H  C.sub.2 H.sub.5                                                                        -- CH.sub.3                                                                           OCH.sub.3                                    J.sub.3                                                                          0 H   H   --  H   -n-C.sub.3 H.sub.7                                                                    -- CH.sub.3                                                                           CH.sub.3                                     J.sub.3                                                                          0 H   H   --  H   -n-C.sub.3 H.sub.7                                                                    -- CH.sub.3                                                                           OCH.sub.3                                    J.sub.3                                                                          0 H   H   --  H   -n-C.sub.3 H.sub.7                                                                    -- OCH.sub.3                                                                          OCH.sub.3                                    J.sub.3                                                                          0 H   H   --  H   -n-C.sub.3 H.sub.7                                                                    -- Cl  OCH.sub.3                                    J.sub.3                                                                          0 H   H   --  H   -n-C.sub.4 H.sub.9                                                                    -- CH.sub.3                                                                           OCH.sub.3                                    J.sub.3                                                                          0 H   H   --  H  CH.sub.2 CH.sub.2 F                                                                    -- OCH.sub.3                                                                          OCH.sub.3                                    J.sub.3                                                                          0 H   H   --  H  CH.sub.2 CH.sub.2 OCH.sub.3                                                            -- Cl  OCH.sub.3                                    J.sub.3                                                                          0 H   H   --  H  CH.sub.2 CHCH.sub.2                                                                    -- CH.sub.3                                                                           OCH.sub.3                                    J.sub.3                                                                          0 H   H   --  H  CH.sub.2 C CH                                                                          -- OCH.sub.3                                                                          OCH.sub.3                                    J.sub.3                                                                          0 H   H   --  H  C(O)CH.sub.3                                                                           -- CH.sub.3                                                                           OCH.sub.33                                   J.sub.3                                                                          0 H   H   --  H  CO.sub.2 CH.sub.3                                                                      -- OCH.sub.3                                                                          OCH.sub.3                                    J.sub.3                                                                          0 H   H   --  CH.sub.3                                                                          CH.sub.3                                                                               -- NH  OCH.sub.3                                    J.sub.3                                                                          0 H   H   --  C.sub.2 H.sub.5                                                                   CH.sub.3                                                                               -- CH.sub.3                                                                           OCH.sub.3                                    J.sub.3                                                                          0 H   Cl  --  H   -n-C.sub.3 H.sub.7                                                                    -- OCH.sub.3                                                                          OCH.sub.3                                    J.sub.3                                                                          0 H   CH.sub.3                                                                           --  H   -n-C.sub.3 H.sub.7                                                                    -- Cl  OCH.sub.3                                    J.sub.3                                                                          0 H   OCH.sub.3                                                                          --  H   -n-C.sub.3 H.sub.7                                                                    -- CH.sub.3                                                                           OCH.sub.3                                    J.sub.3                                                                          0 Cl  H   --  H   -n-C.sub.3 H.sub.7                                                                    -- OCH.sub.3                                                                          OCH.sub.3                                    J.sub.3                                                                          0 CH.sub.3                                                                           H   --  H   -n-C.sub.3 H.sub.7                                                                    -- Cl  OCH.sub.3                                    J.sub.3                                                                          1 H   H   --  H  H       -- CH.sub.3                                                                           OCH.sub.3                                    J.sub.3                                                                          1 H   H   --  H  H       -- OCH.sub.3                                                                          OCH.sub.3                                    J.sub.3                                                                          1 H   H   --  H  CH.sub.3                                                                               -- Cl  OCH.sub.3                                    J.sub.3                                                                          1 H   H   --  H  CH.sub.3                                                                               -- CH.sub.3                                                                           OCH.sub.3                                    J.sub.3                                                                          1 H   H   --  H   -n-C.sub.3 H.sub.7                                                                    -- OCH.sub.3                                                                          OCH.sub.3                                    J.sub.3                                                                          1 H   H   --  H   -n-C.sub.3 H.sub.7                                                                    -- Cl  OCH.sub.3                                    J.sub.3                                                                          1 H   H   --  H   -n-C.sub.3 H.sub.7                                                                    -- CH.sub.3                                                                           CH.sub.3                                     J.sub.3                                                                          1 H   H   --  H   -n-C.sub.3 H.sub.7                                                                    -- CH.sub.3                                                                           OCH.sub.3                                    J.sub.3                                                                          1 H   H   --  CH.sub.3                                                                          CH.sub.3                                                                               -- OCH.sub.3                                                                          OCH.sub.3                                    J.sub.3                                                                          1 H   Cl  --  H   -n-C.sub.3 H.sub.7                                                                    -- Cl  OCH.sub.3                                    J.sub.3                                                                          1 H   CH.sub.3                                                                           --  H   -n-C.sub.3 H.sub.7                                                                    -- CH.sub.3                                                                           OCH.sub.3                                    J.sub.3                                                                          1 H   OCH.sub.3                                                                          --  H   -n-C.sub.4 H.sub.9                                                                    -- OCH.sub.3                                                                          OCH.sub.3                                    J.sub.3                                                                          1 Cl  H   --  H   -n-C.sub.4 H.sub.9                                                                    -- Cl  OCH.sub.3                                    J.sub.3                                                                          1 CH.sub.3                                                                           H   --  H   -n-C.sub.4 H.sub.9                                                                    -- CH.sub.3                                                                           OCH.sub.3                                    J.sub.4                                                                          0 H   --  H   H  H       -- CH.sub.3                                                                           CH.sub.3                                     J.sub.4                                                                          0 H   --  H   H  H       -- CH.sub.3                                                                           OCH.sub.3                                    J.sub.4                                                                          0 H   --  H   H  H       -- OCH.sub.3                                                                          OCH.sub.3                                    J.sub.4                                                                          0 H   --  H   H  H       -- Cl  OCH.sub.3                                    J.sub.4                                                                          0 H   --  H   H  CH.sub.3                                                                               -- CH.sub.3                                                                           CH.sub.3                                     J.sub.4                                                                          0 H   --  H   H  CH.sub.3                                                                               -- CH.sub.3                                                                           OCH.sub.3                                    J.sub.4                                                                          0 H   --  H   H  CH.sub.3                                                                               -- OCH.sub.3                                                                          OCH.sub.3                                    J.sub.4                                                                          0 H   --  H   H  CH.sub.3                                                                               -- Cl  OCH.sub.3                                    J.sub.4                                                                          0 H   --  H   H  C.sub. 2 H.sub.5                                                                       -- CH.sub.3                                                                           OCH.sub.3                                    J.sub.4                                                                          0 H   --  H   H   -n-C.sub.3 H.sub.7                                                                    -- CH.sub.3                                                                           OCH.sub.3                                    J.sub.4                                                                          0 H   --  H   H   -n-C.sub.3 H.sub.7                                                                    -- OCH.sub.3                                                                          OCH.sub.3                                    J.sub.4                                                                          0 H   --  H   H   -n-C.sub.3 H.sub.7                                                                    -- Cl  OCH.sub.3                                    J.sub.4                                                                          0 H   --  H   H   -n-C.sub.4 H.sub.9                                                                    -- CH.sub.3                                                                           CH.sub.3                                     J.sub.4                                                                          0 H   --  H   H   -n-C.sub.4 H.sub.9                                                                    -- CH.sub.3                                                                           OCH.sub.3                                    J.sub.4                                                                          0 H   --  H   H   -n-C.sub.4 H.sub.9                                                                    -- OCH.sub.3                                                                          OCH.sub.3                                    J.sub.4                                                                          0 H   --  H   H   -n-C.sub.4 H.sub.9                                                                    -- Cl  OCH.sub.3                                    J.sub.4                                                                          0 H   --  H   H  CH.sub.2 CH.sub.2 F                                                                    -- CH.sub.3                                                                           OCH.sub.3                                    J.sub.4                                                                          0 H   --  H   H  CH.sub.2 CH.sub.2 OCH.sub.3                                                            -- OCH.sub.3                                                                          OCH.sub.3                                    J.sub.4                                                                          0 H   --  H   H  CH.sub.2 CHCH.sub.2                                                                    -- Cl  OCH.sub.3                                    J.sub.4                                                                          0 H   --  H   H  CH.sub.2 CCH                                                                           -- CH.sub.3                                                                           OCH.sub.3                                    J.sub.4                                                                          0 H   --  H   H  C(O)CH.sub.3                                                                           -- OCH.sub.3                                                                          OCH.sub.3                                    J.sub.4                                                                          0 H   --  H   H  CO.sub.2 CH.sub.3                                                                      -- Cl  OCH.sub.3                                    J.sub.4                                                                          0 H   --  H   CH.sub.3                                                                          H       -- CH.sub.3                                                                           OCH.sub.3                                    J.sub.4                                                                          0 H   --  Cl  H  CH.sub.3                                                                               -- OCH.sub.3                                                                          OCH.sub.3                                    J.sub.4                                                                          0 H   --  CH.sub.3                                                                           H  CH.sub.3                                                                               -- Cl  OCH.sub.3                                    J.sub.4                                                                          0 H   --  OCH.sub.3                                                                          H   -n-C.sub.4 H.sub.9                                                                    -- CH.sub.3                                                                           OCH.sub.3                                    J.sub.4                                                                          0 CH.sub.3                                                                           --  H   H   -n-C.sub.4 H.sub.9                                                                    -- OCH.sub.3                                                                          OCH.sub.3                                    J.sub.4                                                                          0 Cl  --  H   H  H       -- Cl  OCH.sub.3                                    J.sub.4                                                                          0 OCH.sub.3                                                                          --  H   H  CH      -- CH.sub.3                                                                           OCH.sub.3                                    J.sub.4                                                                          0 Cl  --  Cl  H  H       -- OCH.sub.3                                                                          OCH.sub.3                                    J.sub.4                                                                          0 CH.sub.3                                                                           --  CH.sub.3                                                                           H  CH.sub.3                                                                               -- Cl  OCH.sub.3                                    J.sub.4                                                                          1 H   --  H   H  H       -- CH.sub.3                                                                           OCH.sub.3                                    J.sub.4                                                                          1 H   --  H   H  H       -- OCH.sub.3                                                                          OCH.sub.3                                    J.sub.4                                                                          1 H   --  H   H  CH.sub.3                                                                               -- Cl  OCH.sub.3                                    J.sub.4                                                                          1 H   --  H   H  CH.sub.3                                                                               -- CH.sub.3                                                                           OCH.sub.3                                    J.sub.4                                                                          1 H   --  H   H  C.sub.2 H.sub.5                                                                        -- OCH.sub.3                                                                          OCH.sub.3                                    J.sub.4                                                                          1 H   --  H   H   -n-C.sub.3 H.sub.7                                                                    -- Cl  OCH.sub.3                                    J.sub.4                                                                          1 H   --  H   H   -n-C.sub.4 H.sub.9                                                                    -- CH.sub.3                                                                           OCH.sub.3                                    J.sub.4                                                                          1 H   --  H   CH.sub.3                                                                          H       -- OCH.sub.3                                                                          OCH.sub.3                                    J.sub.4                                                                          1 H   --  Cl  H  CH.sub.3                                                                               -- Cl  OCH.sub.3                                    J.sub.4                                                                          1 H   --  CH.sub.3                                                                           H   -n-C.sub.3 H.sub.7                                                                    -- CH.sub.3                                                                           OCH.sub.3                                    J.sub.4                                                                          1 H   --  OCH.sub.3                                                                          H   -n-C.sub.4 H.sub.9                                                                    -- OCH.sub.3                                                                          OCH.sub.3                                    J.sub.4                                                                          1 Cl  --  H   H  H       -- Cl  OCH.sub.3                                    J.sub.4                                                                          1 OCH.sub.3                                                                          --  H   H  CH.sub.3                                                                               -- CH.sub.3                                                                           OCH.sub.3                                    J.sub.4                                                                          1 CH.sub.3                                                                           --  H   H   -n-C.sub.3 H.sub.7                                                                    -- OCH.sub.3                                                                          OCH.sub.3                                    J.sub.4                                                                          1 Cl  --  Cl  H   -n-C.sub.3 H.sub.7                                                                    -- Cl  OCH.sub.3                                    J.sub.4                                                                          1 CH.sub.3                                                                           --  CH.sub.3                                                                           H  H       -- CH.sub.3                                                                           OCH.sub.3                                    J.sub.5                                                                          --                                                                               H   H   --  -- --      H  CH.sub.3                                                                           CH.sub.3                                     J.sub.5                                                                          --                                                                               H   H   --  -- --      H  OCH.sub.3                                                                          OCH.sub.3                                    J.sub.5                                                                          --                                                                               H   H   --  -- --      H  OCH.sub.3                                                                          OCH.sub.3                                    J.sub.5                                                                          --                                                                               H   H   --  -- --      H  Cl  OCH.sub.3                                    J.sub.5                                                                          --                                                                               H   H   --  -- --      CH.sub. 3                                                                         CH.sub.3                                                                           OCH.sub.3                                    J.sub.5                                                                          --                                                                               H   Cl  --  -- --      H  OCH.sub.3                                                                          OCH.sub.3                                    J.sub.5                                                                          --                                                                               H   CH.sub.3                                                                           --  -- --      H  Cl  OCH.sub.3                                    J.sub.5                                                                          --                                                                               H   OCH.sub.3                                                                          --  -- --      H  CH.sub.3                                                                           OCH.sub.3                                    J.sub.5                                                                          --                                                                               Cl  H   --  -- --      H  OCH.sub.3                                                                          OCH.sub.3                                    J.sub.5                                                                          --                                                                               CH.sub.3                                                                           H   --  -- --      H  Cl  OCH.sub.3                                    J.sub.6                                                                          --                                                                               H   --  H   -- --      H  CH.sub.3                                                                           CH.sub.3                                     J.sub.6                                                                          --                                                                               H   --  H   -- --      H  CH.sub.3                                                                           OCH.sub.3                                    J.sub.6                                                                          --                                                                               H   --  H   -- --      H  OCH.sub.3                                                                          OCH.sub.3                                    J.sub.6                                                                          --                                                                               H   --  H   -- --      H  Cl  OCH.sub.3                                    J.sub.6                                                                          --                                                                               H   --  H   -- --      CH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                    J.sub.6                                                                          --                                                                               H   --  Cl  -- --      H  OCH.sub.3                                                                          OCH.sub.3                                    J.sub.6                                                                          --                                                                               H   --  CH.sub.3                                                                           -- --      H  Cl  OCH.sub.3                                    J.sub.6                                                                          --                                                                               H   --  OCH.sub.3                                                                          -- --      H  CH.sub.3                                                                           OCH.sub.3                                    J.sub.6                                                                          --                                                                               Cl  --  H   -- --      H  OCH.sub.3                                                                          OCH.sub.3                                    J.sub.6                                                                          --                                                                               CH.sub.3                                                                           --  H   -- --      H  Cl  OCH.sub.3                                    J.sub.6                                                                          --                                                                               Cl  --  Cl  -- --      H  CH.sub.3                                                                           OCH.sub.3                                    __________________________________________________________________________

                                      TABLE 2a                                     __________________________________________________________________________      ##STR54##                                                                     J q R.sub.1                                                                            R.sub.2                                                                            R.sub.3                                                                            R.sub.4                                                                           R.sub.6 R.sub.7                                                                           X    Y    m.p. (°C.)                      __________________________________________________________________________     J.sub.3                                                                          0 H   H   --  H  H       -- CH.sub.3                                                                            CH.sub.3                                    J.sub.3                                                                          0 H   H   --  H  H       -- CH.sub.3                                                                            OCH.sub.3                                   J.sub.3                                                                          0 H   H   --  H  H       -- NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.3                                                                          0 H   H   --  H  CH.sub.3                                                                               -- CH.sub.3                                                                            OCH.sub.3                                   J.sub.3                                                                          0 H   H   --  H  CH.sub.3                                                                               -- CH.sub.3                                                                            CH.sub.3                                    J.sub.3                                                                          0 H   H   --  H  CH.sub.3                                                                               -- OCH.sub.3                                                                           OCH.sub.3                                   J.sub.3                                                                          0 H   H   --  H  CH.sub.3                                                                               -- OCH.sub.3                                                                           OCH.sub.3                                   J.sub.3                                                                          0 H   H   --  H  CH.sub.3                                                                               -- NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.3                                                                          0 H   H   --  H  C.sub.2 H.sub.5                                                                        -- CH.sub.3                                                                            OCH.sub.3                                   J.sub.3                                                                          0 H   H   --  H   -n-C.sub.3 H.sub.7                                                                    -- CH.sub.3                                                                            CH.sub.3                                    J.sub.3                                                                          0 H   H   --  H   -n-C.sub.3 H.sub.7                                                                    -- CH.sub.3                                                                            OCH.sub.3                                   J.sub.3                                                                          0 H   H   --  H   -n-C.sub.3 H.sub.7                                                                    -- OCH.sub.3                                                                           OCH.sub.3                                   J.sub.3                                                                          0 H   H   --  H   -n-C.sub.3 H.sub.7                                                                    -- NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.3                                                                          0 H   H   --  H   -n-C.sub.4 H.sub.9                                                                    -- CH.sub.3                                                                            OCH.sub.3                                   J.sub.3                                                                          0 H   H   --  H  CH.sub.2 CH.sub.2 F                                                                    -- OCH.sub.3                                                                           OCH.sub.3                                   J.sub.3                                                                          0 H   H   --  H  CH.sub.2 CH.sub.2 OCH.sub.3                                                            -- NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.3                                                                          0 H   H   --  H  CH.sub.2 CHCH.sub.2                                                                    -- CH.sub.3                                                                            OCH.sub.3                                   J.sub.3                                                                          0 H   H   --  H  CH.sub.2 CCH                                                                           -- OCH.sub.3                                                                           OCH.sub.3                                   J.sub.3                                                                          0 H   H   --  H  C(O)CH.sub.3                                                                           -- CH.sub.3                                                                            OCH.sub.3                                   J.sub.3                                                                          0 H   H   --  H  CO.sub.2 CH.sub.3                                                                      -- OCH.sub.3                                                                           OCH.sub.3                                   J.sub.3                                                                          0 H   H   --  CH.sub.3                                                                          CH.sub.3                                                                               -- NH   OCH.sub.3                                   J.sub.3                                                                          0 H   H   --  C.sub.2 H.sub.5                                                                   CH.sub.3                                                                               -- CH.sub.3                                                                            OCH.sub.3                                   J.sub.3                                                                          0 H   Cl  --  H   -n-C.sub.3 H.sub.7                                                                    -- OCH.sub.3                                                                           OCH.sub.3                                   J.sub.3                                                                          0 H   CH.sub.3                                                                           --  H   -n-C.sub.3 H.sub.7                                                                    -- NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.3                                                                          0 H   OCH.sub.3                                                                          --  H   -n-C.sub.3 H.sub.7                                                                    -- CH.sub.3                                                                            OCH.sub.3                                   J.sub.3                                                                          0 Cl  H   --  H   -n-C.sub.3 H.sub.7                                                                    -- OCH.sub.3                                                                           OCH.sub.3                                   J.sub.3                                                                          0 CH.sub.3                                                                           H   --  H   -n-C.sub.3 H.sub.7                                                                    -- NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.3                                                                          1 H   H   --  H  H       -- CH.sub.3                                                                            OCH.sub.3                                   J.sub.3                                                                          1 H   H   --  H  H       -- OCH.sub.3                                                                           OCH.sub.3                                   J.sub.3                                                                          1 H   H   --  H  CH.sub.3                                                                               -- NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.3                                                                          1 H   H   --  H  CH.sub.3                                                                               -- CH.sub.3                                                                            OCH.sub.3                                   J.sub.3                                                                          1 H   H   --  H   -n-C.sub.3 H.sub.7                                                                    -- OCH.sub.3                                                                           OCH.sub.3                                   J.sub.3                                                                          1 H   H   --  H   -n-C.sub.3 H.sub.7                                                                    -- NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.3                                                                          1 H   H   --  H   -n-C.sub.3 H.sub.7                                                                    -- CH.sub.3                                                                            CH.sub.3                                    J.sub.3                                                                          1 H   H   --  H   -n-C.sub.3 H.sub.7                                                                    -- CH.sub.3                                                                            OCH.sub.3                                   J.sub.3                                                                          1 H   H   --  CH.sub.3                                                                          CH.sub.3                                                                               -- OCH.sub.3                                                                           OCH.sub.3                                   J.sub.3                                                                          1 H   Cl  --  H    -n-C.sub.3 H.sub.7                                                                   -- NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.3                                                                          1 H   CH.sub.3                                                                           --  H   -n-C.sub.3 H.sub.7                                                                    -- CH.sub.3                                                                            OCH.sub.3                                   J.sub.3                                                                          1 H   OCH.sub.3                                                                          --  H   -n-C.sub.4 H.sub.9                                                                    -- OCH.sub.3                                                                           OCH.sub.3                                   J.sub.3                                                                          1 Cl  H   --  H   -n-C.sub.4 H.sub.9                                                                    -- NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.3                                                                          1 CH.sub.3                                                                           H   --  H   -n-C.sub.4 H.sub.9                                                                    -- CH.sub.3                                                                            OCH.sub.3                                   J.sub.4                                                                          0 H   --  H   H  H       -- CH.sub.3                                                                            CH.sub.3                                    J.sub.4                                                                          0 H   --  H   H  H       -- CH.sub.3                                                                            OCH.sub.3                                   J.sub.4                                                                          0 H   --  H   H  H       -- OCH.sub.3                                                                           OCH.sub.3                                   J.sub.4                                                                          0 H   --  H   H  H       -- NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.4                                                                          0 H   --  H   H  CH.sub.3                                                                               -- CH.sub.3                                                                            CH.sub.3                                    J.sub.4                                                                          0 H   --  H   H  CH.sub.3                                                                               -- CH.sub.3                                                                            OCH.sub. 3                                  J.sub.4                                                                          0 H   --  H   H  CH.sub.3                                                                               -- OCH.sub.3                                                                           OCH.sub.3                                   J.sub.4                                                                          0 H   --  H   H  CH.sub.3                                                                               -- NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.4                                                                          0 H   --  H   H  C.sub.2 H.sub.5                                                                        -- CH.sub.3                                                                            OCH.sub.3                                   J.sub.4                                                                          0 H   --  H   H   -n-C.sub.3 H.sub.7                                                                    -- CH.sub.3                                                                            OCH.sub.3                                   J.sub.4                                                                          0 H   --  H   H   -n-C.sub.3 H.sub.7                                                                    -- OCH.sub.3                                                                           OCH.sub.3                                   J.sub.4                                                                          0 H   --  H   H   -n-C.sub.3 H.sub.7                                                                    -- NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.4                                                                          0 H   --  H   H   -n-C.sub.4 H.sub.9                                                                    -- CH.sub.3                                                                            CH.sub.3                                    J.sub.4                                                                          0 H   --  H   H   -n-C.sub.4 H.sub.9                                                                    -- CH.sub.3                                                                            OCH.sub.3                                   J.sub.4                                                                          0 H   --  H   H   -n-C.sub.4 H.sub.9                                                                    -- OCH.sub.3                                                                           OCH.sub.3                                   J.sub.4                                                                          0 H   --  H   H   -n-C.sub. 4 H.sub.9                                                                   -- NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.4                                                                          0 H   --  H   H  CH.sub.2 CH.sub.2 F                                                                    -- CH.sub.3                                                                            OCH.sub.3                                   J.sub.4                                                                          0 H   --  H   H  CH.sub.2 CH.sub.2 OCH.sub.3                                                            -- OCH.sub.3                                                                           OCH.sub.3                                   J.sub.4                                                                          0 H   --  H   H  CH.sub.2 CHCH.sub.2                                                                    -- NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.4                                                                          0 H   --  H   H  CH.sub.2 CCH                                                                           -- CH.sub.3                                                                            OCH.sub.3                                   J.sub.4                                                                          0 H   --  H   H  C(O)CH.sub.3                                                                           -- OCH.sub.3                                                                           OCH.sub.3                                   J.sub.4                                                                          0 H   --  H   H  CO.sub.2 CH.sub.3                                                                      -- NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.4                                                                          0 H   --  H   CH.sub.3                                                                          H       -- CH.sub.3                                                                            OCH.sub.3                                   J.sub.4                                                                          0 H   --  Cl  H  CH.sub.3                                                                               -- OCH.sub.3                                                                           OCH.sub.3                                   J.sub.4                                                                          0 H   --  CH.sub.3                                                                           H  CH.sub.3                                                                               -- NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.4                                                                          0 H   --  OCH.sub.3                                                                          H   -n-C.sub.4 H.sub.9                                                                    -- CH.sub.3                                                                            OCH.sub.3                                   J.sub.4                                                                          0 CH.sub.3                                                                           --  H   H   -n-C.sub.4 H.sub.9                                                                    -- OCH.sub.3                                                                           OCH.sub.3                                   J.sub.4                                                                          0 Cl  --  H   H  H       -- NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.4                                                                          0 OCH.sub.3                                                                          --  H   H  CH      -- CH.sub.3                                                                            OCH.sub.3                                   J.sub.4                                                                          0 Cl  --  Cl  H  H       -- OCH.sub.3                                                                           OCH.sub.3                                   J.sub.4                                                                          0 CH.sub.3                                                                           --  CH.sub.3                                                                           H  CH.sub.3                                                                               -- NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.4                                                                          1 H   --  H   H  H       -- CH.sub.3                                                                            OCH.sub.3                                   J.sub.4                                                                          1 H   --  H   H  H       -- OCH.sub.3                                                                           OCH.sub.3                                   J.sub.4                                                                          1 H   --  H   H  CH.sub.3                                                                               -- NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.4                                                                          1 H   --  H   H  CH.sub.3                                                                               -- CH.sub.3                                                                            OCH.sub.3                                   J.sub.4                                                                          1 H   --  H   H  C.sub.2 H.sub.5                                                                        -- OCH.sub.3                                                                           OCH.sub.3                                   J.sub.4                                                                          1 H   --  H   H   -n-C.sub.3 H.sub.7                                                                    -- NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.4                                                                          1 H   --  H   H   -n-C.sub.4 H.sub.9                                                                    -- CH.sub.3                                                                            OCH.sub.3                                   J.sub.4                                                                          1 H   --  H   CH.sub.3                                                                          H       -- OCH.sub.3                                                                           OCH.sub.3                                   J.sub.4                                                                          1 H   --  Cl  H  CH.sub.3                                                                               -- NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.4                                                                          1 H   --  CH.sub.3                                                                           H   -n-C.sub.3 H.sub.7                                                                    -- CH.sub.3                                                                            OCH.sub.3                                   J.sub.4                                                                          1 H   --  OCH.sub.3                                                                          H   -n-C.sub.4 H.sub.9                                                                    -- OCH.sub.3                                                                           OCH.sub.3                                   J.sub.4                                                                          1 Cl  --  H   H  H       -- NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.4                                                                          1 OCH.sub.3                                                                          --  H   H  CH.sub.3                                                                               -- CH.sub.3                                                                            OCH.sub.3                                   J.sub.4                                                                          1 CH.sub.3                                                                           --  H   H   -n-C.sub.3 H.sub.7                                                                    -- OCH.sub.3                                                                           OCH.sub.3                                   J.sub.4                                                                          1 Cl  --  Cl  H   -n-C.sub.3 H.sub.7                                                                    -- NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.4                                                                          1 CH.sub.3                                                                           --  CH.sub.3                                                                           H  H       -- CH.sub.3                                                                            OCH.sub.3                                   J.sub.5                                                                          --                                                                               H   H   --  -- --      H  CH.sub.3                                                                            CH.sub.3                                    J.sub.5                                                                          --                                                                               H   H   --  -- --      H  OCH.sub.3                                                                           OCH.sub.3                                   J.sub.5                                                                          --                                                                               H   H   --  -- --      H  OCH.sub.3                                                                           OCH.sub.3                                   J.sub.5                                                                          --                                                                               H   H   --  -- --      H  NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.5                                                                          --                                                                               H   H   --  -- --      CH.sub.3                                                                          CH.sub.3                                                                            OCH.sub.3                                   J.sub.5                                                                          --                                                                               H   Cl  --  -- --      H  OCH.sub.3                                                                           OCH.sub.3                                   J.sub.5                                                                          --                                                                               H   CH.sub.3                                                                           --  -- --      H  NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.5                                                                          --                                                                               H   OCH.sub.3                                                                          --  -- --      H  CH.sub.3                                                                            OCH.sub.3                                   J.sub.5                                                                          --                                                                               Cl  H   --  -- --      H  OCH.sub.3                                                                           OCH.sub.3                                   J.sub.5                                                                          --                                                                               CH.sub.3                                                                           H   --  -- --      H  NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.6                                                                          --                                                                               H   --  H   -- --      H  CH.sub.3                                                                            CH.sub. 3                                   J.sub.6                                                                          --                                                                               H   --  H   -- --      H  CH.sub.3                                                                            OCH.sub.3                                   J.sub.6                                                                          --                                                                               H   --  H   -- --      H  OCH.sub.3                                                                           OCH.sub.3                                   J.sub.6                                                                          --                                                                               H   --  H   -- --      H  NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.6                                                                          --                                                                               H   --  H   -- --      CH.sub.3                                                                          CH.sub.3                                                                            OCH.sub.3                                   J.sub.6                                                                          --                                                                               H   --  Cl  -- --      H  OCH.sub.3                                                                           OCH.sub.3                                   J.sub.6                                                                          --                                                                               H   --  CH.sub.3                                                                           -- --      H  NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.6                                                                          --                                                                               H   --  OCH.sub.3                                                                          -- --      H  CH.sub.3                                                                            OCH.sub.3                                   J.sub.6                                                                          --                                                                               Cl  --  H   -- --      H  OCH.sub.3                                                                           OCH.sub.3                                   J.sub.6                                                                          --                                                                               CH.sub.3                                                                           --  H   -- --      H  NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.6                                                                          --                                                                               Cl  --  Cl  -- --      H  CH.sub.3                                                                            OCH.sub.3                                   __________________________________________________________________________

                  TABLE 3                                                          ______________________________________                                          ##STR55##                                                                                                                m.p.                                JqQ.sub.1                                                                              R.sub.1 R.sub.2 R.sub.3                                                                              R.sub.17 R.sub.18                                                                     X     Y(°C.)                       ______________________________________                                         J.sub.7 0O                                                                             H       H       --    HH     CH.sub.3                                                                             CH.sub.3                            J.sub.7 0O                                                                             H       H       --    HH     CH.sub.3                                                                             OCH.sub.3                           J.sub.7 0O                                                                             H       H       --    HH     OCH.sub.3                                                                            OCH.sub.3                           J.sub.7 0O                                                                             H       H       --    HH     Cl    OCH.sub.3                           J.sub.7 0O                                                                             H       H       --    HCH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                           J.sub.7 0O                                                                             H       H       --    CH.sub.3 CH.sub.3                                                                     OCH.sub.3                                                                            OCH.sub.3                           J.sub.7 0O                                                                             H       Cl      --    HH     Cl    OCH.sub.3                           J.sub.7 0O                                                                             H       CH.sub.3                                                                               --    HH     CH.sub.3                                                                             OCH.sub.3                           J.sub.7 0O                                                                             H       OCH.sub.3                                                                              --    HH     OCH.sub.3                                                                            OCH.sub.3                           J.sub.7 0O                                                                             Cl      H       --    HH     Cl    OCH.sub.3                           J.sub.7 0O                                                                             CH      H       --    HH     OCH.sub.3                                                                            OCH.sub.3                           J.sub.7 0S                                                                             H       H       --    HH     CH.sub.3                                                                             CH.sub.3                            J.sub.7 0S                                                                             H       H       --    HH     CH.sub.3                                                                             OCH.sub.3                           J.sub.7 0S                                                                             H       H       --    HH     OCH.sub.3                                                                            OCH.sub.3                           J.sub.7 0S                                                                             H       H       --    HH     Cl    OCH.sub.3                           J.sub.7 0S                                                                             H       H       --    HCH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                           J.sub.7 0S                                                                             H       H       --    CH.sub.3 CH.sub.3                                                                     OCH.sub.3                                                                            OCH.sub.3                           J.sub.7 0S                                                                             H       Cl      --    HH     Cl    OCH.sub.3                           J.sub.7 0S                                                                             H       OCH.sub.3                                                                              --    HH     CH.sub.3                                                                             OCH.sub.3                           J.sub.7 0S                                                                             H       CH.sub.3                                                                               --    HH     OCH.sub.3                                                                            OCH.sub.3                           J.sub.7 0S                                                                             Cl      H       --    HH     Cl    OCH.sub.3                           J.sub.7 0S                                                                             CH.sub.3                                                                               H       --    HH     CH.sub.3                                                                             OCH.sub.3                           J.sub.7 0SO.sub.2                                                                      H       H       --    HH     OCH.sub.3                                                                            OCH.sub.3                           J.sub.7 0SO.sub.2                                                                      H       H       --    HH     CH.sub.3                                                                             OCH.sub.3                           J.sub.7 0SO.sub.2                                                                      H       H       --    HH     OCH.sub.3                                                                            OCH.sub.3                           J.sub.7 0SO.sub.2                                                                      H       H       --    HCH.sub.3                                                                             Cl    OCH.sub.3                           J.sub.7 0SO.sub.2                                                                      H       Cl      --    HH     CH.sub.3                                                                             OCH.sub.3                           J.sub.7 0SO.sub.2                                                                      H       CH.sub.3                                                                               --    HH     OCH.sub.3                                                                            OCH.sub.3                           J.sub.7 0SO.sub.2                                                                      H       OCH.sub.3                                                                              --    HH     Cl    OCH.sub.3                           J.sub.7 0SO.sub.2                                                                      Cl      H       --    HH     CH.sub.3                                                                             OCH.sub.3                           J.sub.7 0SO.sub.2                                                                      OCH.sub.3                                                                              H       --    HH     OCH.sub.3                                                                            OCH.sub.3                           J.sub.7 0NH                                                                            H       H       --    HH     Cl    OCH.sub.3                           J.sub.7 0NH                                                                            H       H       --    HH     CH.sub.3                                                                             OCH.sub.3                           J.sub.7 0NH                                                                            H       H       --    HCH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                           J.sub.7 0NCH.sub.3                                                                     H       H       --    HH     Cl    OCH.sub.3                           J.sub.7 0NCH.sub.3                                                                     H       H       --    HH     CH.sub.3                                                                             OCH.sub.3                           J.sub.7 0NCH.sub.3                                                                     H       H       --    HCH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                           J.sub.7 1O                                                                             H       H       --    HH     Cl    OCH.sub.3                           J.sub.7 1O                                                                             H       H       --    HH     CH.sub.3                                                                             OCH.sub.3                           J.sub.7 1O                                                                             H       H       --    HH     OCH.sub.3                                                                            OCH.sub.3                           J.sub.7 1O                                                                             H       H       --    HCH.sub.3                                                                             Cl    OCH.sub.3                           J.sub.7 1O                                                                             H       H       --    CH.sub.3 CH.sub.3                                                                     CH.sub.3                                                                             OCH.sub.3                           J.sub.7 1S                                                                             H       H       --    HH     OCH.sub.3                                                                            OCH.sub.3                           J.sub.7 1S                                                                             H       H       --    HCH.sub.3                                                                             Cl    OCH.sub.3                           J.sub.7 1SO.sub.2                                                                      H       H       --    HH     CH.sub.3                                                                             OCH.sub.3                           J.sub.7 1SO.sub.2                                                                      H       H       --    HH     OCH.sub.3                                                                            OCH.sub.3                           J.sub.7 1SO.sub.2                                                                      H       H       --    HCH.sub.3                                                                             Cl    OCH.sub.3                           J.sub.7 H1SO.sub.2                                                                             H       --    CH.sub.3 CH.sub.3                                                                     CH.sub.3                                                                             OCH.sub.3                           J.sub.7 1NH                                                                            H       H       --    HH     OCH.sub.3                                                                            OCH.sub.3                           J.sub.7 1NCH.sub.3                                                                     H       H       --    HH     Cl    OCH.sub.3                           J.sub.8 0O                                                                             H       --      H     HH     CH.sub.3                                                                             CH.sub.3                            J.sub.8 0O                                                                             H       --      H     HH     CH.sub.3                                                                             OCH.sub.3                           J.sub.8 0O                                                                             H       --      H     HH     OCH.sub.3                                                                            OCH.sub.3                           J.sub.8 0O                                                                             H       --      H     HH     Cl    OCH.sub.3                           J.sub.8 0O                                                                             H       --      H     HCH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                           J.sub.8 0O                                                                             H       --      H     CH.sub.3 CH.sub.3                                                                     OCH.sub.3                                                                            OCH.sub.3                           J.sub.8 0O                                                                             H       --      Cl    HH     Cl    OCH.sub.3                           J.sub.8 0O                                                                             H       --      OCH.sub.3                                                                            HH     CH.sub.3                                                                             OCH.sub.3                           J.sub.8 0O                                                                             H       --      CH.sub.3                                                                             HH     OCH.sub.3                                                                            OCH.sub.3                           J.sub.8 0O                                                                             Cl      --      H     HH     Cl    OCH.sub.3                           J.sub. 8 0O                                                                            CH      --      H     HH     CH.sub.3                                                                             OCH.sub.3                           J.sub.8 0S                                                                             H       --      H     HH     OCH.sub.3                                                                            OCH.sub.3                           J.sub.8 0S                                                                             H       --      H     HH     Cl    OCH.sub.3                           J.sub.8 0SO.sub.2                                                                      H       --      H     HH     CH.sub.3                                                                             OCH.sub.3                           J.sub.8 0SO.sub.2                                                                      H       --      H     HH     OCH.sub.3                                                                            OCH.sub.3                           J.sub.8 0SO.sub.2                                                                      H       --      H     HH     Cl    OCH.sub.3                           J.sub.8 0SO.sub.2                                                                      H       --      H     HCH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                           J.sub.8 0SO.sub.2                                                                      H       --      H     HCH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                           J.sub.8 0SO.sub.2                                                                      H       --      H     HCH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                           J.sub.8 0SO.sub.2                                                                      H       --      H     HCH.sub.2                                                                             Cl    OCH.sub.3                           J.sub.8 0SO.sub.2                                                                      H       --      H     CH.sub.3 CH.sub.3                                                                     CH.sub.3                                                                             OCH.sub.3                           J.sub.8 0NH                                                                            H       --      H     HH     OCH.sub.3                                                                            OCH.sub.3                           J.sub.8 0NCH.sub.3                                                                     H       --      H     HH     Cl    OCH.sub.3                           J.sub.8 0NCH.sub.3                                                                     H       --      H     HH     CH.sub.3                                                                             OCH.sub.3                           J.sub.8 1O                                                                             H       --      H     HH     CH.sub.3                                                                             CH.sub.3                            J.sub.8 1O                                                                             H       --      H     HH     CH.sub.3                                                                             OCH.sub.3                           J.sub.8 1O                                                                             H       --      H     HH     OCH.sub.3                                                                            OCH.sub.3                           J.sub.8 1O                                                                             H       --      H     HH     Cl    OCH.sub.3                           J.sub.8 1O                                                                             H       --      H     HCH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                           J.sub.8 1S                                                                             H       --      H     HH     OCH.sub.3                                                                            OCH.sub.3                           J.sub.8 1SO                                                                            H       --      H     HH     Cl    OCH.sub.3                           J.sub.8 1SO.sub.2                                                                      H       --      H     HH     CH.sub.3                                                                             OCH.sub.3                           J.sub.8 1SO.sub.2                                                                      H       --      H     HCH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                           J.sub.8 1NH                                                                            H       --      H     HH     Cl    OCH.sub.3                           J.sub.8 1NCH.sub.3                                                                     H       --      H     HH     CH.sub.3                                                                             OCH.sub.3                           J.sub.8 1NCH.sub.3                                                                     H       --      H     HCH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                           ______________________________________                                    

                                      TABLE 3a                                     __________________________________________________________________________      ##STR56##                                                                     J  q  Q.sub.1                                                                            R.sub.1                                                                            R.sub.2                                                                            R.sub.3                                                                            R.sub.17                                                                           R.sub.18                                                                           X    Y    m.p. (°C.)                      __________________________________________________________________________     J.sub.7                                                                           0  O   H   H   --  H   H   CH.sub.3                                                                            CH.sub.3                                    J.sub.7                                                                           0  O   H   H   --  H   H   CH.sub.3                                                                            OCH.sub.3                                   J.sub.7                                                                           0  O   H   H   --  H   H   OCH.sub.3                                                                           OCH.sub.3                                   J.sub.7                                                                           0  O   H   H   --  H   H   NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.7                                                                           0  O   H   H   --  H   CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                                   J.sub.7                                                                           0  O   H   H   --  CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                   J.sub.7                                                                           0  O   H   Cl  --  H   H   NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.7                                                                           0  O   H   CH.sub.3                                                                           --  H   H   CH.sub.3                                                                            OCH.sub.3                                   J.sub.7                                                                           0  O   H   OCH.sub.3                                                                          --  H   H   OCH.sub.3                                                                           OCH.sub.3                                   J.sub.7                                                                           0  O   Cl  H   --  H   H   NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.7                                                                           0  O   CH  H   --  H   H   OCH.sub.3                                                                           OCH.sub.3                                   J.sub.7                                                                           0  S   H   H   --  H   H   CH.sub.3                                                                            CH.sub.3                                    J.sub.7                                                                           0  S   H   H   --  H   H   CH.sub.3                                                                            OCH.sub.3                                   J.sub.7                                                                           0  S   H   H   --  H   H   OCH.sub.3                                                                           OCH.sub.3                                   J.sub.7                                                                           0  S   H   H   --  H   H   NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.7                                                                           0  S   H   H   --  H   CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                                   J.sub.7                                                                           0  S   H   H   --  CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                   J.sub.7                                                                           0  S   H   Cl  --  H   H   NHCH.sub.2                                                                          CH.sub.2 CH.sub.3                           J.sub.7                                                                           0  S   H   OCH.sub.3                                                                          --  H   H   CH.sub.3                                                                            OCH.sub.3                                   J.sub.7                                                                           0  S   H   CH.sub.3                                                                           --  H   H   OCH.sub.3                                                                           OCH.sub.3                                   J.sub.7                                                                           0  S   Cl  H   --  H   H   NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.7                                                                           0  S   CH.sub.3                                                                           H   --  H   H   CH.sub.3                                                                            OCH.sub.3                                   J.sub.7                                                                           0  SO.sub.2                                                                           H   H   --  H   H   OCH.sub.3                                                                           OCH.sub.3                                   J.sub.7                                                                           0  SO.sub.2                                                                           H   H   --  H   H   CH.sub.3                                                                            OCH.sub.3                                   J.sub.7                                                                           0  SO.sub.2                                                                           H   H   --  H   H   OCH.sub.3                                                                           OCH.sub.3                                   J.sub.7                                                                           0  SO.sub.2                                                                           H   H   --  H   CH.sub.3                                                                           NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.7                                                                           0  SO.sub.2                                                                           H   Cl  --  H   H   CH.sub.3                                                                            OCH.sub.3                                   J.sub.7                                                                           0  SO.sub.2                                                                           H   CH.sub.3                                                                           --  H   H   OCH.sub.3                                                                           OCH.sub.3                                   J.sub.7                                                                           0  SO.sub.2                                                                           H   OCH.sub.3                                                                          --  H   H   NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.7                                                                           0  SO.sub.2                                                                           Cl  H   --  H   H   CH.sub.3                                                                            OCH.sub.3                                   J.sub.7                                                                           0  SO.sub.2                                                                           OCH.sub.3                                                                          H   --  H   H   OCH.sub.3                                                                           OCH.sub.3                                   J.sub.7                                                                           0  NH  H   H   --  H   H   NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.7                                                                           0  NH  H   H   --  H   H   CH.sub.3                                                                            OCH.sub.3                                   J.sub.7                                                                           0  NH  H   H   --  H   CH.sub. 3                                                                          OCH.sub.3                                                                           OCH.sub.3                                   J.sub.7                                                                           0  NCH.sub.3                                                                          H   H   --  H   H   NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.7                                                                           0  NCH.sub.3                                                                          H   H   --  H   H   CH.sub.3                                                                            OCH.sub.3                                   J.sub.7                                                                           0  NCH.sub.3                                                                          H   H   --  H   CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                   J.sub.7                                                                           1  O   H   H   --  H   H   NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.7                                                                           1  O   H   H   --  H   H   CH.sub.3                                                                            OCH.sub.3                                   J.sub.7                                                                           1  O   H   H   --  H   H   OCH.sub.3                                                                           OCH.sub.3                                   J.sub.7                                                                           1  O   H   H   --  H   CH.sub.3                                                                           NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.7                                                                           1  O   H   H   --  CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                                   J.sub.7                                                                           1  S   H   H   --  H   H   OCH.sub.3                                                                           OCH.sub.3                                   J.sub.7                                                                           1  S   H   H   --  H   CH.sub.3                                                                           NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.7                                                                           1  SO.sub.2                                                                           H   H   --  H   H   CH.sub.3                                                                            OCH.sub.3                                   J.sub.7                                                                           1  SO.sub.2                                                                           H   H   --  H   H   OCH.sub.3                                                                           OCH.sub.3                                   J.sub.7                                                                           1  SO.sub.2                                                                           H   H   --  H   CH.sub.3                                                                           NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.7                                                                           1  SO.sub.2                                                                           H   H   --  CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                                   J.sub.7                                                                           1  NH  H   H   --  H   H   OCH.sub.3                                                                           OCH.sub.3                                   J.sub.7                                                                           1  NCH.sub.3                                                                          H   H   --  H   H   NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.8                                                                           0  O   H   --  H   H   H   CH.sub.3                                                                            CH.sub.3                                    J.sub.8                                                                           0  O   H   --  H   H   H   CH.sub.3                                                                            OCH.sub.3                                   J.sub.8                                                                           0  O   H   --  H   H   H   OCH.sub.3                                                                           OCH.sub.3                                   J.sub.8                                                                           0  O   H   --  H   H   H   NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.8                                                                           0  O   H   --  H   H   CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                                   J.sub.8                                                                           0  O   H   --  H   CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                   J.sub.8                                                                           0  O   H   --  Cl  H   H   NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.8                                                                           0  O   H   --  OCH.sub.3                                                                          H   H   CH.sub.3                                                                            OCH.sub.3                                   J.sub.8                                                                           0  O   H   --  CH.sub.3                                                                           H   H   OCH.sub.3                                                                           OCH.sub.3                                   J.sub.8                                                                           0  O   Cl  --  H   H   H   NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.8                                                                           0  O   CH  --  H   H   H   CH.sub.3                                                                            OCH.sub.3                                   J.sub.8                                                                           0  S   H   --  H   H   H   OCH.sub.3                                                                           OCH.sub.3                                   J.sub.8                                                                           0  S   H   --  H   H   H   NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.8                                                                           0  SO.sub.2                                                                           H   --  H   H   H   CH.sub.3                                                                            OCH.sub.3                                   J.sub.8                                                                           0  SO.sub.2                                                                           H   --  H   H   H   OCH.sub.3                                                                           OCH.sub.3                                   J.sub.8                                                                           0  SO.sub.2                                                                           H   --  H   H   H   NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.8                                                                           0  SO.sub.2                                                                           H   --  H   H   CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                                   J.sub.8                                                                           0  SO.sub.2                                                                           H   --  H   H   CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                   J.sub.8                                                                           0  SO.sub.2                                                                           H   --  H   H   CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                   J.sub.8                                                                           0  SO.sub.2                                                                           H   --  H   H   CH.sub.2                                                                           NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.8                                                                           0  SO.sub.2                                                                           H   --  H   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                                   J.sub.8                                                                           0  NH  H   --  H   H   H   OCH.sub.3                                                                           OCH.sub.3                                   J.sub.8                                                                           0  NCH.sub.3                                                                          H   --  H   H   H   NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.8                                                                           0  NCH.sub.3                                                                          H   --  H   H   H   CH.sub.3                                                                            OCH.sub.3                                   J.sub.8                                                                           1  O   H   --  H   H   H   CH.sub.3                                                                            CH.sub.3                                    J.sub.8                                                                           1  O   H   --  H   H   H   CH.sub.3                                                                            OCH.sub.3                                   J.sub.8                                                                           1  O   H   --  H   H   H   OCH.sub.3                                                                           OCH.sub.3                                   J.sub.8                                                                           1  O   H   --  H   H   H   NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.8                                                                           1  O   H   --  H   H   CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                                   J.sub.8                                                                           1  S   H   --  H   H   H   OCH.sub.3                                                                           OCH.sub.3                                   J.sub.8                                                                           1  SO  H   --  H   H   H   NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.8                                                                           1  SO.sub.2                                                                           H   --  H   H   H   CH.sub.3                                                                            OCH.sub.3                                   J.sub.8                                                                           1  SO.sub.2                                                                           H   --  H   H   CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                   J.sub.8                                                                           1  NH  H   --  H   H   H   NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                           J.sub.8                                                                           1  NCH.sub.3                                                                          H   --  H   H   H   CH.sub.3                                                                            OCH.sub.3                                   J.sub.8                                                                           1  NCH.sub.3                                                                          H   --  H   H   CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                   __________________________________________________________________________

                  TABLE 4                                                          ______________________________________                                          ##STR57##                                                                     J   q     R.sub.1                                                                              R.sub.2                                                                            R.sub.3                                                                             R.sub.19                                                                            R.sub.20                                                                            X     Y     m.p. (°C.)               ______________________________________                                         J.sub.9                                                                            0     H     H   --   H    H    CH.sub.3                                                                             CH.sub.3                              J.sub.9                                                                            0     H     H   --   H    H    CH.sub.3                                                                             OCH.sub.3                             J.sub.9                                                                            0     H     H   --   H    H    OCH.sub.3                                                                            OCH.sub.3                             J.sub.9                                                                            0     H     H   --   Cl   Cl   CH.sub.3                                                                             OCH.sub.3                             J.sub.9                                                                            0     H     H   --   Cl   Cl   OCH.sub.3                                                                            OCH.sub.3                             J.sub.9                                                                            0     H     H   --   Cl   Cl   Cl    OCH.sub.3                             J.sub.9                                                                            0     H     H   --   CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                             OCH.sub.3                             J.sub.9                                                                            0     H     H   --   CH.sub.3                                                                            CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                             J.sub.9                                                                            1     H     H   --   H    H    Cl    OCH.sub.3                             J.sub.9                                                                            1     H     H   --   Cl   Cl   CH.sub.3                                                                             OCH.sub.3                             J.sub.9                                                                            1     H     H   --   CH.sub.3                                                                            CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                             J.sub.10                                                                           0     H     --  H    H    H    Cl    OCH.sub.3                             J.sub.10                                                                           0     H     --  H    H    H    CH    OCH.sub.3                             J.sub.10                                                                           0     H     --  H    H    H    OCH.sub.3                                                                            OCH.sub.3                             J.sub.10                                                                           0     H     --  H    Cl   Cl   Cl    OCH.sub.3                             J.sub.10                                                                           0     H     --  H    Cl   Cl   CH.sub.3                                                                             OCH.sub.3                             J.sub.10                                                                           0     H     --  H    Cl   Cl   OCH.sub.3                                                                            OCH.sub.3                             J.sub.10                                                                           0     H     --  H    CH.sub.3                                                                            CH.sub.3                                                                            Cl    OCH.sub.3                             J.sub.10                                                                           1     H     --  H    H    H    CH.sub.3                                                                             OCH.sub.3                             J.sub.10                                                                           1     H     --  H    Cl   Cl   OCH.sub.3                                                                            OCH.sub.3                             J.sub.10                                                                           1     H     --  H    CH.sub.3                                                                            CH.sub.3                                                                            Cl    OCH.sub.3                             ______________________________________                                    

                  TABLE 4a                                                         ______________________________________                                          ##STR58##                                                                                                                       m.p.                         J   q     R.sub.1                                                                              R.sub.2                                                                            R.sub.3                                                                            R.sub.19                                                                             R.sub.20                                                                             X      Y      (°C.)                 ______________________________________                                         J.sub.9                                                                            0     H     H   --  H     H     CH.sub.3                                                                              CH.sub.3                            J.sub.9                                                                            0     H     H   --  H     H     CH.sub.3                                                                              OCH.sub.3                           J.sub.9                                                                            0     H     H   --  H     H     OCH.sub.3                                                                             OCH.sub.3                           J.sub.9                                                                            0     H     H   --  H     H     NHCH.sub.3                                                                            CH.sub.2 CH.sub.3                   J.sub.9                                                                            0     H     H   --  Cl    Cl    CH.sub.3                                                                              OCH.sub.3                           J.sub.9                                                                            0     H     H   --  Cl    Cl    OCH.sub.3                                                                             OCH.sub.3                           J.sub.9                                                                            0     H     H   --  Cl    Cl    NHCH.sub.3                                                                            CH.sub.2 CH.sub.3                   J.sub.9                                                                            0     H     H   --  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                              OCH.sub. 3                          J.sub.9                                                                            0     H     H   --  CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                             OCH.sub.3                           J.sub.9                                                                            1     H     H   --  H     H     NHCH.sub.3                                                                            CH.sub.2 CH.sub.3                   J.sub.9                                                                            1     H     H   --  Cl    Cl    CH.sub.3                                                                              OCH.sub.3                           J.sub.9                                                                            1     H     H   --  CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                             OCH.sub.3                           J.sub.10                                                                           0     H     --  H   H     H     NHCH.sub.3                                                                            CH.sub.2 CH.sub.3                   J.sub.10                                                                           0     H     --  H   H     H     CH.sub.3                                                                              OCH.sub.3                           J.sub.10                                                                           0     H     --  H   H     H     OCH.sub.3                                                                             OCH.sub.3                           J.sub.10                                                                           0     H     --  H   Cl    Cl    NHCH.sub.3                                                                            CH.sub.2 CH.sub.3                   J.sub.10                                                                           0     H     --  H   Cl    Cl    CH.sub.3                                                                              OCH.sub.3                           J.sub.10                                                                           0     H     --  H   Cl    Cl    OCH.sub.3                                                                             OCH.sub.3                           J.sub.10                                                                           0     H     --  H   CH.sub.3                                                                             CH.sub.3                                                                             NHCH.sub.3                                                                            CH.sub.2 CH.sub.3                   J.sub.10                                                                           1     H     --  H   H     H     CH.sub.3                                                                              OCH.sub.3                           J.sub.10                                                                           1     H     --  H   Cl    Cl    OCH.sub.3                                                                             OCH.sub.3                           J.sub.10                                                                           1     H     --  H   CH.sub.3                                                                             CH.sub.3                                                                             NHCH.sub.3                                                                            CH.sub.2 CH.sub.                    ______________________________________                                                                                    3                              

                  TABLE 5                                                          ______________________________________                                          ##STR59##                                                                     J   R.sub.1                                                                               R.sub.2                                                                               R.sub.3                                                                            R.sub.5                                                                             R.sub.6                                                                              X     Y     m.p. (°C.)                 ______________________________________                                         J.sub.11                                                                           H      H      --  H    H     CH.sub.3                                                                             OCH.sub.3                               J.sub.11                                                                           H      CH.sub.3                                                                              --  H    H     OCH.sub.3                                                                            OCH.sub.3                               J.sub.11                                                                           H      H      --  H    CH.sub.3                                                                             Cl    OCH.sub.3                               J.sub.11                                                                           H      Cl     --  H    CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                J.sub.11                                                                           CH.sub.3                                                                              H      --  H    C.sub.2 H.sub.5                                                                      CH.sub.3                                                                             OCH.sub.3                               J.sub.11                                                                           H      H      --  H     -n-C.sub.3 H.sub.7                                                                  OCH.sub.3                                                                            OCH.sub.3                               J.sub.11                                                                           H      H      --  H     -n-C.sub.4 H.sub.9                                                                  Cl    OCH.sub.3                               J.sub.11                                                                           H      H      --  CH.sub.3                                                                            H     CH.sub.3                                                                             OCH.sub.3                               J.sub.11                                                                           H      H      --  CH.sub.3                                                                            CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                               J.sub.12                                                                           H      --     H   H    H     Cl    OCH.sub.3                               J.sub.12                                                                           Cl     --     Cl  H    H     CH.sub.3                                                                             OCH.sub.3                               J.sub.12                                                                           H      --     H   H    CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                               J.sub.12                                                                           H      --     H   H    CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                J.sub.12                                                                           H      --     H   H    C.sub.2 H.sub.5                                                                      CH.sub.3                                                                             OCH.sub.3                               J.sub.12                                                                           H      --     H   H     -n-C.sub.3 H.sub.7                                                                  OCH.sub.3                                                                            OCH.sub.3                               J.sub.12                                                                           H      --     H   H     -n-C.sub.4 H.sub.9                                                                  Cl    OCH.sub.3                               J.sub.12                                                                           H      --     H   CH.sub.3                                                                            H     CH.sub.3                                                                             OCH.sub.3                               J.sub.12                                                                           H      --     H   CH.sub.3                                                                            CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                               J.sub.26                                                                           H      H      --  CH.sub.3                                                                            --    OCH.sub.3                                                                            OCH.sub.3                               J.sub.26                                                                           H      H      --  CH.sub.3                                                                            --    OCH.sub.3                                                                            CH.sub.3                                J.sub.26                                                                           H      H      --  CH.sub.3                                                                            --    OCH.sub.3                                                                            Cl                                      J.sub.26                                                                           H      H      --  CH.sub.3                                                                            --    CH.sub.3                                                                             CH.sub.3                                J.sub.26                                                                           H      H      --  H    --    OCH.sub.3                                                                            OCH.sub.3                               J.sub.26                                                                           H      H      --  H    --    OCH.sub.3                                                                            CH.sub.3                                J.sub.26                                                                           H      Cl     --  CH.sub.3                                                                            --    OCH.sub.3                                                                            OCH.sub.3                               J.sub.27                                                                           H      --     H   CH.sub.3                                                                            --    OCH.sub.3                                                                            OCH.sub.3                               J.sub.27                                                                           H      --     H   CH.sub.3                                                                            --    OCH.sub.3                                                                            CH.sub.3                                J.sub.27                                                                           H      --     H   CH.sub.3                                                                            --    OCH.sub.3                                                                            Cl                                      J.sub.27                                                                           H      --     H   CH.sub.3                                                                            --    CH.sub.3                                                                             CH.sub.3                                J.sub.27                                                                           H      --     H   H    --    OCH.sub.3                                                                            OCH.sub.3                               J.sub.27                                                                           H      --     H   H    --    OCH.sub.3                                                                            CH.sub.3                                J.sub.27                                                                           H      --     Cl  CH.sub.3                                                                            --    OCH.sub.3                                                                            OCH.sub.3                               J.sub.28                                                                           H      H      --  CH.sub.3                                                                            --    OCH.sub.3                                                                            OCH.sub.3                               J.sub.28                                                                           H      H      --  CH.sub.3                                                                            --    OCH.sub.3                                                                            CH.sub.3                                J.sub.28                                                                           H      H      --  CH.sub.3                                                                            --    OCH.sub.3                                                                            Cl                                      J.sub.28                                                                           H      H      --  CH.sub.3                                                                            --    CH.sub.3                                                                             CH.sub.3                                J.sub.28                                                                           H      H      --  H    --    OCH.sub.3                                                                            OCH.sub.3                               J.sub.28                                                                           H      H      --  H    --    OCH.sub.3                                                                            CH.sub.3                                J.sub.28                                                                           H      Cl     --  CH.sub.3                                                                            --    OCH.sub. 3                                                                           OCH.sub.3                               J.sub.29                                                                           H      --     H   CH.sub.3                                                                            --    OCH.sub.3                                                                            OCH.sub.3                               J.sub.29                                                                           H      --     H   CH.sub.3                                                                            --    OCH.sub.3                                                                            CH.sub.3                                J.sub.29                                                                           H      --     H   CH.sub.3                                                                            --    OCH.sub.3                                                                            Cl                                      J.sub.29                                                                           H      --     H   CH.sub.3                                                                            --    CH.sub.3                                                                             CH.sub.3                                J.sub.29                                                                           H      --     H   H    --    OCH.sub.3                                                                            OCH.sub.3                               J.sub.29                                                                           H      --     H   H    --    OCH.sub.3                                                                            CH.sub.3                                J.sub.29                                                                           H      --     Cl  CH.sub.3                                                                            --    OCH.sub.3                                                                            OCH.sub.3                               ______________________________________                                    

                  TABLE 5a                                                         ______________________________________                                          ##STR60##                                                                                                                     m.p.                           J    R.sub.1                                                                               R.sub.2                                                                               R.sub.3                                                                            R.sub.5                                                                             R.sub.6                                                                              X      Y      (°C.)                   ______________________________________                                         J.sub.11                                                                            H      H      --  H    H     CH.sub.3                                                                              OCH.sub.3                             J.sub.11                                                                            H      CH.sub.3                                                                              --  H    H     OCH.sub.3                                                                             OCH.sub.3                             J.sub.11                                                                            H      H      --  H    CH.sub.3                                                                             NHCH.sub.3                                                                            CH.sub.2 CH.sub.3                     J.sub.11                                                                            H      Cl     --  H    CH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3                              J.sub.11                                                                            CH.sub.3                                                                              H      --  H    C.sub.2 H.sub.5                                                                      CH.sub.3                                                                              OCH.sub.3                             J.sub.11                                                                            H      H      --  H     -n-C.sub.3 H.sub.7                                                                  OCH.sub.3                                                                             OCH.sub.3                             J.sub.11                                                                            H      H      --  H     -n-C.sub.4 H.sub.9                                                                  NHCH.sub.3                                                                            CH.sub.2 CH.sub.3                     J.sub.11                                                                            H      H      --  CH.sub.3                                                                            H     CH.sub.3                                                                              OCH.sub.3                             J.sub.11                                                                            H      H      --  CH.sub.3                                                                            CH.sub.3                                                                             OCH.sub.3                                                                             OCH.sub.3                             J.sub.12                                                                            H      --     H   H    H     NHCH.sub.3                                                                            CH.sub.2 CH.sub.3                     J.sub.12                                                                            Cl     --     Cl  H    H     CH.sub.3                                                                              OCH.sub.3                             J.sub.12                                                                            H      --     H   H    CH.sub.3                                                                             OCH.sub.3                                                                             OCH.sub.3                             J.sub.12                                                                            H      --     H   H    CH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3                              J.sub.12                                                                            H      --     H   H    C.sub.2 H.sub.5                                                                      CH.sub.3                                                                              OCH.sub.3                             J.sub.12                                                                            H      --     H   H     -n-C.sub.3 H.sub.7                                                                  OCH.sub.3                                                                             OCH.sub.3                             J.sub.12                                                                            H      --     H   H     -n-C.sub.4 H.sub.9                                                                  NHCH.sub.3                                                                            CH.sub.2 CH.sub.3                     J.sub.12                                                                            H      --     H   CH.sub.3                                                                            H     CH.sub.3                                                                              OCH.sub.3                             J.sub.12                                                                            H      --     H   CH.sub.3                                                                            CH.sub.3                                                                             OCH.sub.3                                                                             OCH.sub.3                             J.sub.26                                                                            H      H      --  CH.sub.3                                                                            --    OCH.sub.3                                                                             OCH.sub.3                             J.sub.26                                                                            H      H      --  CH.sub.3                                                                            --    OCH.sub.3                                                                             CH.sub.3                              J.sub.26                                                                            H      H      --  CH.sub.3                                                                            --    CH.sub.3                                                                              CH.sub.3                              J.sub.26                                                                            H      H      --  H    --    OCH.sub.3                                                                             OCH.sub.3                             J.sub.26                                                                            H      H      --  H    --    OCH.sub.3                                                                             CH.sub.3                              J.sub.26                                                                            H      Cl     --  CH.sub.3                                                                            --    OCH.sub.3                                                                             OCH.sub.3                             J.sub.26                                                                            Cl     H      --  CH.sub.3                                                                            --    OCH.sub.3                                                                             OCH.sub.3                             J.sub.27                                                                            H      --     H   CH.sub.3                                                                            --    OCH.sub.3                                                                             OCH.sub.3                             J.sub.27                                                                            H      --     H   CH.sub.3                                                                            --    OCH.sub.3                                                                             CH.sub.3                              J.sub.27                                                                            H      --     H   CH.sub.3                                                                            --    CH.sub.3                                                                              CH.sub.3                              J.sub.27                                                                            H      --     H   H    --    OCH.sub.3                                                                             OCH.sub.3                             J.sub.27                                                                            H      --     H   H    --    OCH.sub.3                                                                             CH.sub.3                              J.sub.27                                                                            H      --     Cl  CH.sub.3                                                                            --    OCH.sub.3                                                                             OCH.sub.3                             J.sub.27                                                                            Cl     --     H   CH.sub.3                                                                            --    OCH.sub.3                                                                             OCH.sub.3                             J.sub.28                                                                            H      H      --  CH.sub.3                                                                            --    OCH.sub.3                                                                             OCH.sub.3                             J.sub.28                                                                            H      H      --  CH.sub.3                                                                            --    OCH.sub.3                                                                             CH.sub.3                              J.sub.28                                                                            H      H      --  CH.sub.3                                                                            --    CH.sub.3                                                                              CH.sub.3                              J.sub.28                                                                            H      H      --  H    --    OCH.sub. 3                                                                            OCH.sub.3                             J.sub.28                                                                            H      H      --  H    --    OCH.sub.3                                                                             CH.sub.3                              J.sub.28                                                                            H      Cl     --  CH.sub.3                                                                            --    OCH.sub.3                                                                             OCH.sub.3                             J.sub.28                                                                            Cl     H      --  CH.sub.3                                                                            --    OCH.sub.3                                                                             OCH.sub.3                             J.sub.29                                                                            H      --     H   CH.sub.3                                                                            --    OCH.sub.3                                                                             OCH.sub.3                             J.sub.29                                                                            H      --     H   CH.sub.3                                                                            --    OCH.sub.3                                                                             CH.sub.3                              J.sub.29                                                                            H      --     H   CH.sub.3                                                                            --    CH.sub.3                                                                              CH.sub.3                              J.sub.29                                                                            H      --     H   H    --    OCH.sub.3                                                                             OCH.sub.3                             J.sub.29                                                                            H      --     H   H    --    OCH.sub.3                                                                             CH.sub.3                              J.sub.29                                                                            H      --     Cl  CH.sub.3                                                                            --    OCH.sub.3                                                                             OCH.sub.3                             J.sub.29                                                                            Cl     --     H   CH.sub.3                                                                            --    OCH.sub.3                                                                             OCH.sub.3                             ______________________________________                                    

                  TABLE 6                                                          ______________________________________                                          ##STR61##                                                                                                                       m.p.                         J    q     Q.sub.1 R.sub.1                                                                             R.sub.2                                                                            R.sub.3                                                                            R.sub.7                                                                             X      Y     (°C.)                 ______________________________________                                         J.sub.13                                                                            0     O       H    H   --  H    CH.sub.3                                                                              OCH.sub.3                          J.sub.13                                                                            0     O       H    Cl  --  H    OCH.sub.3                                                                             OCH.sub.3                          J.sub.13                                                                            0     O       H    H   --  CH.sub.3                                                                            Cl     OCH.sub.3                          J.sub.13                                                                            1     O       H    H   --  H    CH.sub.3                                                                              OCH.sub.3                          J.sub.13                                                                            1     O       H    H   --  CH.sub.3                                                                            OCH.sub.3                                                                             OCH.sub.3                          J.sub.13                                                                            1     O       CH.sub.3                                                                            H   --  H    Cl     OCH.sub.3                          J.sub.13                                                                            0     S       H    H   --  H    CH.sub.3                                                                              CH.sub.3                           J.sub.13                                                                            0     SO      H    H   --  H    CH.sub.3                                                                              OCH.sub.3                          J.sub.13                                                                            0     SO.sub.2                                                                               H    H   --  H    OCH.sub. 3                                                                            OCH.sub.3                          J.sub.13                                                                            0     S       H    H   --  H    Cl     OCH.sub.3                          J.sub.13                                                                            1     SO      H    H   --  H    CH.sub.3                                                                              OCH.sub.3                          J.sub.13                                                                            1     SO.sub.2                                                                               H    H   --  H    OCH.sub.3                                                                             OCH.sub.3                          J.sub.13                                                                            1     NH      H    H   --  H    Cl     OCH.sub.3                          J.sub.13                                                                            1     NCH.sub.3                                                                              H    H   --  H    CH.sub.3                                                                              OCH.sub.3                          J.sub.13                                                                            1     NH      H    H   --  H    OCH.sub.3                                                                             OCH.sub.3                          J.sub.13                                                                            1     NCH.sub.3                                                                              H    H   --  H    Cl     OCH.sub.3                          J.sub.14                                                                            0     O       H    --  H   H    CH.sub.3                                                                              OCH.sub.3                          J.sub.14                                                                            0     O       H    --  H   H    OCH.sub.3                                                                             OCH.sub.3                          J.sub.14                                                                            1     O       H    --  H   CH.sub.3                                                                            Cl     OCH.sub.3                          J.sub.14                                                                            1     O       Cl   --  Cl  H    CH.sub.3                                                                              OCH.sub.3                          J.sub.14                                                                            0     S       H    --  H   H    OCH.sub.3                                                                             OCH.sub.3                          J.sub.14                                                                            0     SO.sub.2                                                                               H    --  H   H    Cl     OCH.sub.3                          J.sub.14                                                                            1     S       H    --  H   H    CH.sub.3                                                                              OCH.sub.3                          J.sub.14                                                                            1     SO.sub.2                                                                               H    --  H   H    OCH.sub.3                                                                             OCH.sub.3                          J.sub. 14                                                                           0     NCH.sub.3                                                                              H    --  H   H    Cl     OCH.sub.3                          ______________________________________                                    

                  TABLE 6a                                                         ______________________________________                                          ##STR62##                                                                                                                       m.p.                         J   q     Q.sub.1 R.sub.1                                                                             R.sub.2                                                                            R.sub.3                                                                            R.sub.7                                                                             X      Y      (°C.)                 ______________________________________                                         J.sub.13                                                                           0     O       H    H   --  H    CH.sub.3                                                                              OCH.sub.3                           J.sub.13                                                                           0     O       H    Cl  --  H    OCH.sub.3                                                                             OCH.sub.3                           J.sub.13                                                                           0     O       H    H   --  CH.sub.3                                                                            NHCH.sub.3                                                                            CH.sub.2 CH.sub.3                   J.sub.13                                                                           1     O       H    H   --  H    CH.sub.3                                                                              OCH.sub.3                           J.sub.13                                                                           1     O       H    H   --  CH.sub.3                                                                            OCH.sub.3                                                                             OCH.sub.3                           J.sub.13                                                                           1     O       CH.sub.3                                                                            H   --  H    NHCH.sub.3                                                                            CH.sub.2 CH.sub.3                   J.sub.13                                                                           0     S       H    H   --  H    CH.sub.3                                                                              CH.sub.3                            J.sub.13                                                                           0     SO      H    H   --  H    CH.sub.3                                                                              OCH.sub. 3                          J.sub.13                                                                           0     SO.sub.2                                                                               H    H   --  H    OCH.sub.3                                                                             OCH.sub.3                           J.sub.13                                                                           0     S       H    H   --  H    NHCH.sub.3                                                                            CH.sub.2 CH.sub.3                   J.sub.13                                                                           1     SO      H    H   --  H    CH.sub.3                                                                              OCH.sub.3                           J.sub.13                                                                           1     SO.sub.2                                                                               H    H   --  H    OCH.sub.3                                                                             OCH.sub.3                           J.sub.13                                                                           1     NH      H    H   --  H    NHCH.sub.3                                                                            CH.sub.2 CH.sub.3                   J.sub.13                                                                           1     NCH.sub.3                                                                              H    H   --  H    CH.sub.3                                                                              OCH.sub.3                           J.sub.13                                                                           1     NH      H    H   --  H    OCH.sub.3                                                                             OCH.sub.3                           J.sub.13                                                                           1     NCH.sub.3                                                                              H    H   --  H    NHCH.sub.3                                                                            CH.sub.2 CH.sub.3                   J.sub.14                                                                           0     O       H    --  H   H    CH.sub.3                                                                              OCH.sub.3                           J.sub.14                                                                           0     O       H    --  H   H    OCH.sub.3                                                                             OCH.sub.3                           J.sub.14                                                                           1     O       H    --  H   CH.sub.3                                                                            NHCH.sub.3                                                                            CH.sub.2 CH.sub.3                   J.sub.14                                                                           1     O       Cl   --  Cl  H    CH.sub.3                                                                              OCH.sub.3                           J.sub.14                                                                           0     S       H    --  H   H    OCH.sub.3                                                                             OCH.sub.3                           J.sub.14                                                                           0     SO.sub.2                                                                               H    --  H   H    NHCH.sub.3                                                                            CH.sub.2 CH.sub.3                   J.sub. 14                                                                          1     S       H    --  H   H    CH.sub.3                                                                              OCH.sub.3                           J.sub.14                                                                           1     SO.sub.2                                                                               H    --  H   H    OCH.sub.3                                                                             OCH.sub.3                           J.sub.14                                                                           0     NCH.sub.3                                                                              H    --  H   H    NHCH.sub.3                                                                            CH.sub.2 CH.sub.3                   ______________________________________                                    

                  TABLE 7                                                          ______________________________________                                          ##STR63##                                                                                                                       m.p.                         J    q     R.sub.1                                                                               R.sub.2                                                                              R.sub.3                                                                            R.sub.21                                                                            R.sub.22                                                                            X     Y     (°C.)                 ______________________________________                                         J.sub.15                                                                            0     H      H     --  H    H    CH.sub.3                                                                             OCH.sub.3                          J.sub.15                                                                            0     H      H     --  H    CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                          J.sub.15                                                                            0     H      H     --  CH.sub.3                                                                            CH.sub.3                                                                            Cl    OCH.sub.3                          J.sub.15                                                                            1     H      Cl    --  H    H    CH.sub.3                                                                             OCH.sub.3                          J.sub.15                                                                            0     H      CH.sub.3                                                                             --  H    H    OCH.sub.3                                                                            OCH.sub.3                          J.sub.15                                                                            0     H      OCH.sub.3                                                                            --  H    H    Cl    OCH.sub.3                          J.sub.15                                                                            0     Cl     H     --  H    H    CH.sub.3                                                                             OCH.sub.3                          J.sub.15                                                                            0     CH.sub.3                                                                              H     --  H    H    OCH.sub.3                                                                            OCH.sub.3                          J.sub.16                                                                            0     H      --    H   H    H    Cl    OCH.sub.3                          J.sub.16                                                                            0     H      --    H   H    CH.sub.3                                                                            CH.sub.3                                                                             CH.sub.3                           J.sub.16                                                                            0     H      --    H   CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                             OCH.sub.3                          J.sub.16                                                                            1     H      --    H   H    H    Cl    OCH.sub.3                          ______________________________________                                    

                  TABLE 7a                                                         ______________________________________                                          ##STR64##                                                                                                                 m.p.                               J   q     R.sub.1                                                                               R.sub.2                                                                              R.sub.3                                                                            R.sub.21                                                                            R.sub.22                                                                            X      Y(°C.)                      ______________________________________                                         J.sub.15                                                                           0     H      H     --  H    H    CH.sub.3                                                                              OCH.sub.3                          J.sub.15                                                                           0     H      H     --  H    CH.sub.3                                                                            OCH.sub.3                                                                             OCH.sub.3                          J.sub.15                                                                           0     H      H     --  CH.sub.3                                                                            CH.sub.3                                                                            NHCH.sub.3                                                                            CH.sub.2 CH.sub.3                  J.sub.15                                                                           1     H      Cl    --  H    H    CH.sub.3                                                                              OCH.sub.3                          J.sub.15                                                                           0     H      CH.sub.3                                                                             --  H    H    OCH.sub.3                                                                             OCH.sub.3                          J.sub.15                                                                           0     H      OCH.sub.3                                                                            --  H    H    NHCH.sub.3                                                                            CH.sub.2 CH.sub.3                  J.sub.15                                                                           0     Cl     H     --  H    H    CH.sub.3                                                                              OCH.sub.3                          J.sub.15                                                                           0     CH.sub.3                                                                              H     --  H    H    OCH.sub. 3                                                                            OCH.sub.3                          J.sub.16                                                                           0     H      --    H   H    H    NHCH.sub.3                                                                            CH.sub.2 CH.sub.3                  J.sub.16                                                                           0     H      --    H   H    CH.sub.3                                                                            CH.sub.3                                                                              CH.sub.3                           J.sub.16                                                                           0     H      --    H   CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                          J.sub.16                                                                           1     H      --    H   H    H    NHCH.sub.3                                                                            CH.sub.2 CH.sub.3                  ______________________________________                                    

                                      TABLE 8                                      __________________________________________________________________________      ##STR65##                                                                     J  Q.sub.2                                                                             Q.sub.3                                                                            R.sub.1                                                                           R.sub.2                                                                           R.sub.3                                                                           R.sub.7                                                                           X   Y   m.p. (°C.)                              __________________________________________________________________________     J.sub.19                                                                          O    --  H  H  -- H  CH.sub.3                                                                           OCH.sub.3                                          J.sub.19                                                                          O    --  H  H  -- H  OCH.sub.3                                                                          OCH.sub.3                                          J.sub.19                                                                          O    --  H  H  -- CH.sub.3                                                                          Cl  OCH.sub.3                                          J.sub.19                                                                          O    --  H  Cl -- H  CH.sub.3                                                                           OCH.sub.3                                          J.sub.19                                                                          S    --  H  H  -- H  OCH.sub.3                                                                          OCH.sub.3                                                                          183-186(d)                                     J.sub.19                                                                          S    --  H  H  -- H  Cl  OCH.sub.3                                                                          169-173(d)                                     J.sub.19                                                                          S    --  H  H  -- CH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                          J.sub.19                                                                          S    --  Cl H  -- H  OCH.sub.3                                                                          OCH.sub.3                                          J.sub.19                                                                          S    --  H  H  -- H  CH.sub.3                                                                           CH.sub.3                                                                           194-196(d)                                     J.sub.19                                                                          S    --  H  H  -- H  CH.sub.3                                                                           OCH.sub.3                                                                          182-184(d)                                     J.sub.19                                                                          NH   --  H  H  -- H  Cl  OCH.sub.3                                          J.sub.19                                                                          NCH.sub.3                                                                           --  H  H  -- H  CH.sub.3                                                                           CH.sub.3                                           J.sub.19                                                                          NCH.sub.3                                                                           --  H  H  -- H  CH.sub.3                                                                           OCH.sub.3                                          J.sub.19                                                                          CH.sub.2                                                                            --  H  H  -- H  OCH.sub.3                                                                          OCH.sub.3                                          J.sub.19                                                                          CH.sub.2                                                                            --  H  H  -- H  Cl  OCH.sub.3                                          J.sub.19                                                                          CHCH.sub.3                                                                          --  H  H  -- H  CH.sub.3                                                                           OCH.sub.3                                          J.sub.20                                                                          O    --  H  -- H  H  OCH.sub.3                                                                          OCH.sub.3                                          J.sub.20                                                                          O    --  H  -- H  H  Cl  OCH.sub.3                                          J.sub.20                                                                          O    --  Cl -- Cl H  CH.sub.3                                                                           OCH.sub.3                                          J.sub.20                                                                          O    --  H  -- H  CH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                          J.sub.20                                                                          S    --  H  -- H  H  Cl  OCH.sub.3                                          J.sub.20                                                                          S    --  H  -- H  H  CH.sub.3                                                                           OCH.sub.3                                          J.sub.20                                                                          S    --  H  -- H  CH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                          J.sub.20                                                                          S    --  Cl -- Cl H  Cl  OCH.sub.3                                          J.sub.20                                                                          NH   --  H  -- H  H  CH.sub.3                                                                           OCH.sub.3                                          J.sub.20                                                                          NCH.sub.3                                                                           --  H  -- H  H  OCH.sub.3                                                                          OCH.sub.3                                          J.sub.20                                                                          NCH.sub.3                                                                           --  H  -- H  H  Cl  OCH.sub.3                                          J.sub.21                                                                          --   O   H  H  -- H  CH.sub.3                                                                           OCH.sub.3                                          J.sub.21                                                                          --   O   H  H  -- CH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                          J.sub.21                                                                          --   O   H  CH.sub.3                                                                          -- H  OCH.sub.3                                                                          OCH.sub.3                                                                          151-158(d)                                     J.sub.21                                                                          --   O   H  CH.sub.3                                                                          -- H  CH.sub.3                                                                           CH.sub.3                                                                           186-188(d)                                     J.sub.21                                                                          --   O   H  CH.sub.3                                                                          -- H  Cl  OCH.sub.3                                                                          164-167(d)                                     J.sub.21                                                                          --   S   H  H  -- H  Cl  OCH.sub.3                                          J.sub.21                                                                          --   S   H  Cl -- H  CH.sub.3                                                                           CH.sub.3                                           J.sub.21                                                                          --   NH  H  H  -- H  CH.sub.3                                                                           OCH.sub.3                                          J.sub.21                                                                          --   NCH.sub.3                                                                          Cl H  -- H  OCH.sub.3                                                                          OCH.sub.3                                          J.sub.21                                                                          --   CH.sub.2                                                                           H  H  -- H  Cl  OCH.sub.3                                          J.sub.22                                                                          --   O   H  -- H  H  CH.sub.3                                                                           OCH.sub.3                                          J.sub.22                                                                          --   O   H  -- H  CH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                          J.sub.22                                                                          --   S   H  -- H  H  Cl  OCH.sub.3                                          J.sub.22                                                                          --   S   H  -- H  Cl CH.sub.3                                                                           OCH.sub.3                                          J.sub.22                                                                          --   NH  H  -- CH.sub.3                                                                          H  OCH.sub.3                                                                          OCH.sub.3                                          J.sub.22                                                                          --   NCH.sub.3                                                                          H  -- H  H  Cl  OCH.sub.3                                          J.sub.22                                                                          --   CH.sub.2                                                                           Cl -- H  H  CH.sub.3                                                                           OCH.sub.3                                          J.sub.22                                                                          --   CH.sub.2                                                                           H  -- H  H  OCH.sub.3                                                                          OCH.sub.3                                          __________________________________________________________________________

                                      TABLE 8a                                     __________________________________________________________________________      ##STR66##                                                                     J  Q.sub.2                                                                             Q.sub.3                                                                            R.sub.1                                                                           R.sub.2                                                                           R.sub.3                                                                           R.sub.7                                                                           X    Y    m.p. (°C.)                            __________________________________________________________________________     J.sub.19                                                                          O    --  H  H  -- H  CH.sub.3                                                                            OCH.sub.3                                         J.sub.19                                                                          O    --  H  H  -- H  OCH.sub.3                                                                           OCH.sub.3                                         J.sub.19                                                                          O    --  H  H  -- CH.sub.3                                                                          NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                                 J.sub.19                                                                          O    --  H  Cl -- H  CH.sub.3                                                                            OCH.sub.3                                         J.sub.19                                                                          S    --  H  H  -- H  OCH.sub.3                                                                           OCH.sub.3                                                                           167-170(d)                                   J.sub.19                                                                          S    --  H  H  -- H  NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                                 J.sub.19                                                                          S    --  H  H  -- CH.sub.3                                                                          CH.sub.3                                                                            OCH.sub.3                                         J.sub.19                                                                          S    --  Cl H  -- H  OCH.sub.3                                                                           OCH.sub.3                                         J.sub.19                                                                          S    --  H  H  -- H  OCH.sub.3                                                                           CH.sub.3                                                                            152-156(d)                                   J.sub.19                                                                          NH   --  H  H  -- H  NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                                 J.sub.19                                                                          NCH.sub.3                                                                           --  H  H  -- H  CH.sub.3                                                                            CH.sub.3                                          J.sub.19                                                                          NCH.sub.3                                                                           --  H  H  -- H  CH.sub.3                                                                            OCH.sub.3                                         J.sub.19                                                                          CH.sub.2                                                                            --  H  H  -- H  OCH.sub.3                                                                           OCH.sub.3                                         J.sub.19                                                                          CH.sub.2                                                                            --  H  H  -- H  NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                                 J.sub.19                                                                          CHCH.sub.3                                                                          --  H  H  -- H  CH.sub.3                                                                            OCH.sub.3                                         J.sub.20                                                                          O    --  H  -- H  H  OCH.sub.3                                                                           OCH.sub.3                                         J.sub.20                                                                          O    --  H  -- H  H  NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                                 J.sub.20                                                                          O    --  Cl -- Cl H  OCH.sub.3                                                                           OCH.sub.3                                         J.sub.20                                                                          O    --  H  -- H  CH.sub.3                                                                          OCH.sub.3                                                                           OCH.sub.3                                         J.sub.20                                                                          S    --  H  -- H  H  NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                                 J.sub.20                                                                          S    --  H  -- H  H  CH.sub.3                                                                            OCH.sub.3                                         J.sub.20                                                                          S    --  H  -- H  CH.sub.3                                                                          OCH.sub.3                                                                           OCH.sub.3                                         J.sub.20                                                                          S    --  Cl -- Cl H  NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                                 J.sub.20                                                                          NH   --  H  -- H  H  CH.sub.3                                                                            OCH.sub.3                                         J.sub.20                                                                          NCH.sub.3                                                                           --  H  -- H  H  OCH.sub.3                                                                           OCH.sub.3                                         J.sub.20                                                                          NCH.sub.3                                                                           --  H  -- H  H  NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                                 J.sub.21                                                                          --   O   H  H  -- H  CH.sub.3                                                                            OCH.sub.3                                         J.sub.21                                                                          --   O   H  H  -- CH.sub.3                                                                          OCH.sub.3                                                                           OCH.sub.3                                         J.sub.21                                                                          --   O   H  CH.sub.3                                                                          -- H  OCH.sub.3                                                                           OCH.sub.3                                                                           151-157(d)                                   J.sub.21                                                                          --   O   H  CH.sub.3                                                                          -- H  OCH.sub.3                                                                           CH.sub.3                                                                            167-172(d)                                   J.sub.21                                                                          --   S   H  H  -- H  NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                                 J.sub.21                                                                          --   S   H  Cl -- H  CH.sub.3                                                                            CH.sub.3                                          J.sub.21                                                                          --   NH  H  H  -- H  CH.sub.3                                                                            OCH.sub.3                                         J.sub.21                                                                          --   NCH.sub.3                                                                          Cl H  -- H  OCH.sub.3                                                                           OCH.sub. 3                                        J.sub.21                                                                          --   CH.sub.2                                                                           H  H  -- H  NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                                 J.sub.22                                                                          --   O   H  -- H  H  CH.sub.3                                                                            OCH.sub.3                                         J.sub.22                                                                          --   O   H  -- H  CH.sub.3                                                                          OCH.sub.3                                                                           OCH.sub.3                                         J.sub.22                                                                          --   S   H  -- H  H  NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                                 J.sub.22                                                                          --   S   H  -- H  Cl CH.sub.3                                                                            OCH.sub.3                                         J.sub.22                                                                          --   NH  H  -- CH.sub.3                                                                          H  OCH.sub.3                                                                           OCH.sub.3                                         J.sub.22                                                                          --   NCH.sub.3                                                                          H  -- H  H  NHCH.sub.3                                                                          CH.sub.2 CH.sub.3                                 J.sub.22                                                                          --   CH.sub.2                                                                           Cl -- H  H  CH.sub.3                                                                            OCH.sub.3                                         J.sub.22                                                                          --   CH.sub.2                                                                           H  -- H  H  OCH.sub.3                                                                           OCH.sub.3                                         __________________________________________________________________________

                  TABLE 9                                                          ______________________________________                                          ##STR67##                                                                     J    R.sub.1                                                                               R.sub.2                                                                               R.sub.3                                                                             R.sub.23                                                                              X     Y     m.p. (°C.)                   ______________________________________                                         J.sub.23                                                                            H      H      --   H      CH.sub.3                                                                             OCH.sub.3                                 J.sub.23                                                                            H      H      --   8-CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                                 J.sub.23                                                                            H      H      --   8-OCH.sub.3                                                                           Cl    OCH.sub.3                                 J.sub.23                                                                            H      H      --   8-Cl   CH.sub.3                                                                             OCH.sub.3                                 J.sub.23                                                                            H      Cl     --   H      OCH.sub.3                                                                            OCH.sub.3                                 J.sub.23                                                                            H      CH.sub.3                                                                              --   H      Cl    OCH.sub.3                                 J.sub.23                                                                            Cl     H      --   H      CH.sub.3                                                                             OCH.sub.3                                 J.sub.24                                                                            H      --     H    H      OCH.sub.3                                                                            OCH.sub.3                                 J.sub.24                                                                            H      --     H    5-CH.sub.3                                                                            Cl    OCH.sub.3                                 J.sub.24                                                                            H      --     H    5-OCH.sub.3                                                                           CH.sub.3                                                                             OCH.sub.3                                 J.sub.24                                                                            H      --     H    5-Cl   OCH.sub.3                                                                            OCH.sub.3                                 J.sub.24                                                                            Cl     --     Cl   H      Cl    OCH.sub.3                                 J.sub.25                                                                            --     H      H    H      CH.sub.3                                                                             OCH.sub.3                                 ______________________________________                                    

                  TABLE 9a                                                         ______________________________________                                          ##STR68##                                                                     J    R.sub.1                                                                              R.sub.2                                                                               R.sub.3                                                                            R.sub.23                                                                              X      Y      m.p. (°C.)                   ______________________________________                                         J.sub.23                                                                            H     H      --  H      CH.sub.3                                                                              OCH.sub.3                                  J.sub.23                                                                            H     H      --  8-CH.sub.3                                                                            OCH.sub.3                                                                             OCH.sub.3                                  J.sub.23                                                                            H     H      --  8-OCH.sub.3                                                                           NHCH.sub.3                                                                            CH.sub.2 CH.sub.3                          J.sub.23                                                                            H     H      --  8-Cl   CH.sub.3                                                                              OCH.sub.3                                  J.sub.23                                                                            H     Cl     --  H      OCH.sub.3                                                                             OCH.sub.3                                  J.sub.23                                                                            H     CH.sub.3                                                                              --  H      NHCH.sub.3                                                                            CH.sub.2 CH.sub.3                          J.sub.23                                                                            Cl    H      --  H      CH.sub.3                                                                              OCH.sub.3                                  J.sub.24                                                                            H     --     H   H      OCH.sub.3                                                                             OCH.sub.3                                  J.sub.24                                                                            H     --     H   5-CH.sub.3                                                                            NHCH.sub.3                                                                            CH.sub.2 CH.sub.3                          J.sub.24                                                                            H     --     H   5-OCH.sub.3                                                                           CH.sub.3                                                                              OCH.sub.3                                  J.sub.24                                                                            H     --     H   5-Cl   OCH.sub.3                                                                             OCH.sub.3                                  J.sub.24                                                                            Cl    --     Cl  H      NHCH.sub.3                                                                            CH.sub.2 CH.sub.3                          J.sub.25                                                                            --    H      H   H      CH.sub.3                                                                              OCH.sub.3                                  ______________________________________                                    

                  TABLE 10                                                         ______________________________________                                          ##STR69##                                                                     ______________________________________                                         where                                                                          J.sub.1a is                                                                          ##STR70##       J.sub.2a is                                                                            ##STR71##                                        J.sub.1b is                                                                          ##STR72##       J.sub.2b is                                                                            ##STR73##                                        J.sub.3a is                                                                          ##STR74##       J.sub.4a is                                                                            ##STR75##                                        J.sub.5a is                                                                          ##STR76##       J.sub.6a is                                                                            ##STR77##                                        J    X           Y             Z     m.p. (°C.)                         ______________________________________                                         J.sub.1a                                                                            OC.sub.2 H.sub.5                                                                           CH.sub.3      CH                                              J.sub.1a                                                                            Br          OCH.sub.3     CH                                              J.sub.1a                                                                            F           OC.sub.2 H.sub.5                                                                             CH                                              J.sub.1a                                                                            I           OCH.sub.3     CH                                              J.sub.1a                                                                            OCF.sub.2 H CH.sub.3      CH                                              J.sub.1a                                                                            CH.sub.2 F  OCH.sub.3     CH                                              J.sub.1a                                                                            CF.sub.3    OCH.sub.3     CH                                              J.sub.1a                                                                            OCH.sub.2 CH.sub.2 F                                                                       CH.sub.3      CH                                              J.sub.1a                                                                            OCH.sub.2 CHF.sub.3                                                                        OCH.sub.3     CH                                              J.sub.1a                                                                            OCH.sub.2 CF.sub.3                                                                         CH.sub. 3     N                                               J.sub.1a                                                                            CH.sub.2 Cl OCH.sub.3     CH                                              J.sub.1a                                                                            CH.sub.2 Br OCH.sub.3     CH                                              J.sub.1a                                                                            OCH.sub.3   H             CH                                              J.sub.1a                                                                            CH.sub.3    OC.sub.2 H.sub.5                                                                             N                                               J.sub.2a                                                                            CH.sub.3    CH.sub.2 OCH.sub.3                                                                           CH                                              J.sub.2a                                                                            OCH.sub.3   NHCH.sub.3    N                                               J.sub.2a                                                                            CH.sub.3    N(OCH.sub.3)CH.sub.3                                                                         N                                               J.sub.2a                                                                            C.sub.2 H.sub.5                                                                            N(CH.sub.3).sub.2                                                                            N                                               J.sub.2a                                                                            OCH.sub.3   CH.sub.2 CH.sub.3                                                                            CH                                              J.sub.3a                                                                            OCH.sub.3   CF.sub.3      CH                                              J.sub.3a                                                                            OCH.sub.3   SCH.sub.3     N                                               J.sub.3a                                                                            CH.sub.3    OCH.sub.2 CHCH.sub.2                                                                         CH                                              J.sub.1b                                                                            CH.sub.3    OCH.sub.2 CCH CH                                              J.sub.1b                                                                            CH.sub.3    CH.sub.2 OCH.sub.2 CH.sub.3                                                                  N                                               J.sub.1b                                                                            CH.sub.3    OCH.sub.2 CH.sub.2 OCH.sub.3                                                                 CH                                              J.sub.2b                                                                            OCH.sub.3   CH.sub.2 SCH.sub.3                                                                           CH                                              J.sub.2b                                                                            OCH.sub.3   CH.sub.2 SCH.sub.2 CH.sub.3                                                                  CH                                              J.sub.2b                                                                            CH.sub.3    C(O)H         CH                                              J.sub.4a                                                                            CH.sub.3    C(O)CH.sub.3  CH                                              J.sub.4a                                                                            CH.sub.3    CH(OCH.sub.3).sub.2                                                                          CH                                              J.sub.5a                                                                            CH.sub.3    1,3-dioxolan-2-yl                                                                            CH                                              J.sub.6a                                                                            CH.sub.3    4-methyl-1,3- CH                                                               dioxolan-2-yl                                                 ______________________________________                                    

                                      TABLE 11                                     __________________________________________________________________________      ##STR78##                                                                     J A  X.sub.1                                                                             Y.sub.1                                                                           X.sub.2                                                                             Y.sub.2                                                                             X.sub.3                                                                            X.sub.4                                                                            Y.sub.3                                                                           Y.sub.4                                                                            Z.sub.1                                                                           m.p. (°C.)                     __________________________________________________________________________     J.sub.1a                                                                         A-2                                                                               CH.sub.3                                                                            O  --   --   --  --  -- --  --                                       J.sub.1a                                                                         A-2                                                                               OCH.sub.3                                                                           O  --   --   --  --  -- --  --                                       J.sub.1b                                                                         A-2                                                                               OC.sub.2 H.sub.5                                                                    O  --   --   --  --  -- --  --                                       J.sub.2a                                                                         A-2                                                                               OCF.sub.2 H                                                                         O  --   --   --  --  -- --  --                                       J.sub.1a                                                                         A-2                                                                               CH.sub.3                                                                            CH.sub.2                                                                          --   --   --  --  -- --  --                                       J.sub.1a                                                                         A-2                                                                               OCH.sub.3                                                                           CH.sub.2                                                                          --   --   --  --  -- --  --                                       J.sub.2b                                                                         A-3                                                                               CH.sub.3                                                                            -- --   --   --  --  -- --  --                                       J.sub.3a                                                                         A-3                                                                               OCH.sub.3                                                                           -- --   --   --  --  -- --  --                                       J.sub.4a                                                                         A-3                                                                               OC.sub.2 H.sub.5                                                                    -- --   --   --  --  -- --  --                                       J.sub.5a                                                                         A-3                                                                               OCF.sub.2 H                                                                         -- --   --   --  --  -- --  --                                       J.sub.1a                                                                         A-4                                                                               CH.sub.3                                                                            -- --   --   --  --  CH.sub.3                                                                          --  --                                       J.sub.1a                                                                         A-4                                                                               OCH.sub.3                                                                           -- --   --   --  --  CH.sub.3                                                                          --  --                                       J.sub.6a                                                                         A-4                                                                               OC.sub.2 H.sub.5                                                                    -- --   --   --  --  CH.sub.3                                                                          --  --                                       J.sub.1b                                                                         A-4                                                                               OCF.sub.2 H                                                                         -- --   --   --  --  CH.sub.3                                                                          --  --                                       J.sub.2a                                                                         A-4                                                                               CH.sub.3                                                                            -- --   --   --  --  H  --  --                                       J.sub.2b                                                                         A-4                                                                               OCH.sub.3                                                                           -- --   --   --  --  H  --  --                                       J.sub.1a                                                                         A-5                                                                               --   -- CH.sub.3                                                                            OCH.sub.3                                                                           --  --  -- --  --                                       J.sub.1a                                                                         A-5                                                                               --   -- C.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                                                                    --  --  -- --  --                                       J.sub.3a                                                                         A-5                                                                               --   -- CH.sub.2 CF.sub.3                                                                   OCH.sub.3                                                                           --  --  -- --  --                                       J.sub.4a                                                                         A-5                                                                               --   -- CH.sub.3                                                                            SCH.sub.3                                                                           --  --  -- --  --                                       J.sub.5a                                                                         A-5                                                                               --   -- CH.sub.3                                                                            SC.sub.2 H.sub.5                                                                    --  --  -- --  --                                       J.sub.6a                                                                         A-5                                                                               --   -- CH.sub.3                                                                            OCF.sub.2 H                                                                         --  --  -- --  --                                       J.sub.1b                                                                         A-5                                                                               --   -- CH.sub.3                                                                            SCF.sub.2 H                                                                         --  --  -- --  --                                       J.sub.1a                                                                         A-5                                                                               --   -- CH.sub.3                                                                            CH.sub.3                                                                            --  --  -- --  --                                       J.sub.1a                                                                         A-5                                                                               --   -- CH.sub.3                                                                            C.sub.2 H.sub.5                                                                     --  --  -- --  --                                       J.sub.1a                                                                         A-6                                                                               --   -- --   --   CH.sub.3                                                                           --  -- --  --                                       J.sub.1a                                                                         A-6                                                                               --   -- --   --   OCH.sub.3                                                                          --  -- --  --                                       J.sub.1a                                                                         A-7                                                                               --   -- --   --   --  OCH.sub.3                                                                          -- OCH.sub.3                                                                          CH                                       J.sub.1a                                                                         A-7                                                                               --   -- --   --   --  CH.sub.3                                                                           -- CH.sub.3                                                                           CH                                       J.sub.1b                                                                         A-7                                                                               --   -- --   --   --  OCH.sub.3                                                                          -- CH.sub.3                                                                           CH                                       J.sub.2a                                                                         A-7                                                                               --   -- --   --   --  OCH.sub.3                                                                          -- OCH.sub.3                                                                          N                                        J.sub.2a                                                                         A-7                                                                               --   -- --   --   --  OCH.sub.3                                                                          -- OCH.sub.3                                                                          CH                                       __________________________________________________________________________      where J.sub.1a, J.sub.1b, J.sub.2a, J.sub.2b, J.sub.3a, J.sub.4a, J.sub.5      and J.sub.6a are as defined in Table 10.                                 

                  TABLE 12                                                         ______________________________________                                          ##STR79##                                                                     where J.sub.1a, J.sub.1b, J.sub.2a, J.sub.2b, J.sub.3a, J.sub.4a,              J.sub.5a and J.sub.6a are                                                      as defined in Table 10.                                                        J         X        Y            Z    m.p. (°C.)                         ______________________________________                                         J.sub.1b  CH.sub.3 CH.sub.3     CH                                             J.sub.2a  CH.sub.3 OCH.sub.3    CH                                             J.sub.1a  OCH.sub.3                                                                               OCH.sub.3    CH                                             J.sub.2b  Cl       OCH.sub.3    CH                                             J.sub.3a  CH.sub.3 CH.sub.3     N                                              J.sub.4a  CH.sub.3 OCH.sub.3    N                                              J.sub.5a  OCH.sub.3                                                                               OCH.sub.3    N                                              J.sub.1a  NHCH.sub.3                                                                              OC.sub.2 H.sub.5                                                                            N                                              J.sub.6a  CH.sub.3 OCH.sub.3    CH                                             ______________________________________                                    

                  TABLE 13                                                         ______________________________________                                          ##STR80##                                                                      ##STR81##                                                                      ##STR82##                                                                     J       X         Y         Z      m.p. (°C.)                           ______________________________________                                         J.sub.5b                                                                               CH.sub.3  CH.sub.3  CH                                                 J.sub.3b                                                                               CH.sub.3  OCH.sub. 3                                                                               CH                                                 J.sub.1c                                                                               OCH.sub.3 OCH.sub.3 CH                                                 J.sub.1c                                                                               Cl        OCH.sub.3 CH                                                 J.sub.5b                                                                               CH.sub.3  CH.sub.3  N                                                  J.sub.3b                                                                               CH.sub.3  OCH.sub.3 N                                                  J.sub.1c                                                                               OCH.sub.3 OCH.sub.3 N                                                  J.sub.1c                                                                               NHCH.sub.3                                                                               OC.sub.2 H.sub.5                                                                         N                                                  J.sub.5b                                                                               OCH.sub.3 OCH.sub.3 CH                                                 ______________________________________                                    

Formulations

Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations, broadly, contain about 0.1% to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 1% to 99.9% solid or liquid inert diluent(s). More specifically, they will contain these ingredients in the following approximate proportions:

                  TABLE 14                                                         ______________________________________                                                     Active  Weight Percent*                                                        Ingredient                                                                             Diluent(s)                                                                               Surfactant(s)                                    ______________________________________                                         Wettable Powders                                                                             20-90      0-74     1-10                                         Oil Suspensions,                                                                              3-50     40-95     0-15                                         Emulsions, Solutions,                                                          (including Emulsifiable                                                        Concentrates)                                                                  Aqueous Suspension                                                                           10-50     40-84     1-20                                         Dusts          1-25     70-99     0-5                                          Granules and Pellets                                                                         0.1-95      5-99.9  0-15                                         High Strength 90-99      0-10     0-2                                          Compositions                                                                   ______________________________________                                          *Active ingredient plus at least one of a surfactant or a diluent equals       100 weight percent.                                                      

Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are sometimes desirable, and are achieved by incorporation into the formulation or by tank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, N.J., but other solids, either mined or manufactured, may be used. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts. Typical liquid diluents and solvents are described in Marsden, "Solvents Guide," 2nd Ed., Interscience, New York, 1950. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0° C. "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood, N.J., as well as Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foaming, caking, corrosion, microbiological growth, etc.

The methods of making such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See J. E. Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York, 1973, pp. 8-57ff.

For further information regarding the art of formulation, see for example:

H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16 through Col. 7, line 19 and Examples 10 through 41;

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182;

H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, June 23, 1959, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4;

G. C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pp. 81-96; and

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.

In the following examples, all parts are by weight unless otherwise indicated.

EXAMPLE 5

Wettable Powder

    ______________________________________                                         N--[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1,3-                                                       80%                                                dihydro-6-methyl-3-oxofuro[3,4-c]pyridine-4-                                   sulfonamide                                                                    sodium alkylnaphthalenesulfonate                                                                           2%                                                 sodium ligninsulfonate      2%                                                 synthetic amorphous silica  3%                                                 kaolinite                   13%                                                ______________________________________                                    

The ingredients are blended, hammer-milled until all the solids are essentially under 50 microns, reblended, and packaged.

EXAMPLE 6

Wettable Powder

    ______________________________________                                         1,3-Dihydro-N--[(4-methoxy-6-methylpyrimidin-2-yl)-                                                        50%                                                aminocarbonyl]-6-methyl-3-oxofuro[3,4-c]pyridine-                              4-sulfonamide                                                                  sodium alkylnaphthalenesulfonate                                                                           2%                                                 low viscosity methyl cellulose                                                                             2%                                                 diatomaceous earth          46%                                                ______________________________________                                    

The ingredients are blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in diameter. The product is reblended before packaging.

EXAMPLE 7

Granule

    ______________________________________                                         Wettable Powder of Example 6                                                                          5%                                                      attapulgite granules  95%                                                      ______________________________________                                    

(U.S.S. 20-40 mesh; 0.84-0.42 mm)

A slurry of wettable powder containing 25% solids is sprayed on the surface of attapulgite granules in a double-cone blender. The granules are dried and packaged.

EXAMPLE 8

Extruded Pellet

    ______________________________________                                         N--[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1,3-                                                       25%                                                dihydro-6-methyl-3-oxofuro[3,4-c]pyridine-4-                                   sulfonamide                                                                    anhydrous sodium sulfate    10%                                                crude calcium ligninsulfonate                                                                               5%                                                sodium alkylnaphthalenesulfonate                                                                            1%                                                calcium/magnesium bentonite 59%                                                ______________________________________                                    

The ingredients are blended, hammer-milled and then moistened with about 12% water. The mixture is extruded as cylinders about 3 mm diameter which are cut to produce pellets about 3 mm long. These may be used directly after drying, or the dried pellets may be crushed to pass a U.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S. No. 40 sieve (0.42 mm openings) may be packaged for use and the fines recycled.

EXAMPLE 9

Low Strength Granule

    ______________________________________                                         N--[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1,3-                                                        0.1%                                              dihydro-6-methyl-3-oxofuro[3,4-c]pyridine-4-                                   sulfonamide                                                                    attapulgite granules        99.9%                                              ______________________________________                                    

(U.S.S. 20-40 mesh)

The active ingredient is dissolved in a solvent and the solution is sprayed upon dedusted granules in a double-cone blender. After spraying of the solution has been completed, the material is warmed to evaporate the solvent. The material is allowed to cool and then packaged.

EXAMPLE 10

Granule

    ______________________________________                                         1,3-Dihydro-N--[(4-methoxy-6-methylpyrimidin-2-yl)-                                                        80%                                                aminocarbonyl]-6-methyl-3-oxofuro 3,4-c]pyridine-                              4-sulfonamide                                                                  wetting agent                1%                                                crude ligninsulfonate salt (containing                                                                     10%                                                5-20% of the natural sugars)                                                   attapulgite clay             9%                                                ______________________________________                                    

The ingredients are blended and milled to pass through a 100 mesh screen. This material is then added to a fluid bed granulator, the air flow is adjusted to gently fluidize the material, and a fine spray of water is sprayed onto the fluidized material. The fluidization and spraying are continued until granules of the desired size range are made. The spraying is stopped, but fluidization is continued, optionally with heat, until the water content is reduced to the desired level, generally less than 1%. The material is then discharged, screened to the desired size range, generally 14-100 mesh (1410-149 microns), and packaged for use.

EXAMPLE 11

Low Strength Granule

    ______________________________________                                         1,3-Dihydro-N--[(4-methoxy-6-methylpyrimidin-2-yl)-                                                        1%                                                 aminocarbonyl]-6-methyl-3-oxofuro[3,4-c]pyridine-                              4-sulfonamide                                                                  N,N--dimethylformamide      9%                                                 attapulgite granules        90%                                                ______________________________________                                    

(U.S.S. 20-40 sieve)

The active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a double cone blender. After spraying of the solution has been completed, the blender is allowed to run for a short period and then the granules are packaged.

EXAMPLE 12

Aqueous Suspension

    ______________________________________                                         N--[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1,3-                                                       40.0%                                              dihydro-6-methyl-3-oxofuro[3,4-c]pyridine-4-                                   sulfonamide                                                                    polyacrylic acid thickener  0.3%                                               dodecylphenol polyethylene glycol ether                                                                    0.5%                                               disodium phosphate          1.0%                                               monosodium phosphate        0.5%                                               polyvinyl alcohol           1.0%                                               water                       56.7%                                              ______________________________________                                    

The ingredients are blended and ground together in a sand mill to produce particles essentially all under 5 microns in size.

EXAMPLE 13

Solution

    ______________________________________                                         1,3-Dihydro-N--[(4-methoxy-6-methylpyrimidin-2-yl)-                                                         5%                                                aminocarbonyl]-6-methyl-3-oxofuro[3,4-c]pyridine-                              4-sulfonamide, sodium salt                                                     water                       95%                                                ______________________________________                                    

The salt is added directly to the water with stirring to produce the solution, which may than be packaged for use.

EXAMPLE 14

High Strength Concentrate

    ______________________________________                                         N--[ (4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1,3-                                                      99.0%                                              dihydro-6-methyl-3-oxofuro[3,4-c]pyridine-4-                                   sulfonamide                                                                    silica aerogel              0.5%                                               synthetic amorphous silica  0.5%                                               ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produce a material essentially all passing a U.S.S. No. 50 screen (0.3 mm opening). The concentrate may be formulated further if necessary.

EXAMPLE 15

Wettable Powder

    ______________________________________                                         1,3-Dihydro-N--[(4-methoxy-6-methylpyrimidin-2-yl)-                                                        90.0%                                              aminocarbonyl]-6-methyl-3-oxofuro[3,4-c]pyridine-                              4-sulfonamide                                                                  dioctyl sodium sulfosuccinate                                                                              0.1%                                               synthetic fine silica       9.9%                                               ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produce particles essentially all below 100 microns. The material is sifted through a U.S.S. No. 50 screen and then packaged.

EXAMPLE 16

Wettable Powder

    ______________________________________                                         N--[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1,3-                                                       40% -dihydro-6-methyl-3-oxofuro[3,4-c]pyridine                                 -4-                                                sulfonamide                                                                    sodium ligninsulfonate      20%                                                montmorillonite clay        40%                                                ______________________________________                                    

The ingredients are thoroughly blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in size. The material is reblended and then packaged.

EXAMPLE 17

Oil Suspension

    ______________________________________                                         1,3-Dihydro-N--[(4-methoxy-6-methylpyrimidin-2-yl)-                                                        35%                                                aminocarbonyl]-6-methyl-3-oxofuro[3,4-c]pyridine-                              4-sulfonamide                                                                  blend of polyalcohol carboxylic                                                                             6%                                                esters and oil soluble petroleum                                               sulfonates                                                                     xylene                      59%                                                ______________________________________                                    

The ingredients are combined and ground together in a sand mill to produce particles essentially all below 5 microns. The product can be used directly, extended with oils, or emulsified in water.

EXAMPLE 18

Dust

    ______________________________________                                         N--[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1,3-                                                       10%                                                dihydro-6-methyl-3-oxofuro[3,4-c]pyridine-4-                                   sulfonamide                                                                    attapulgite                 10%                                                Pyrophyllite                80%                                                ______________________________________                                    

The active ingredient is blended with attapulgite and then passed through a hammer-mill to produce particles substantially all below 200 microns. The ground concentrate is then blended with powdered pyrophyllite until homogeneous.

EXAMPLE 19

Oil Suspension

    ______________________________________                                         1,3-Dihydro-N--[(4-methoxy-6-methylpyrimidin-2-yl)-                                                        25%                                                aminocarbonyl]-6-methyl-3-oxofuro[3,4-c]pyridine-                              4-sulfonamide                                                                  polyoxyethylene sorbitol hexaoleate                                                                         5%                                                highly aliphatic hydrocarbon oil                                                                           70%                                                ______________________________________                                    

The ingredients are ground together in a sand mill until the solid particles have been reduced to under about 5 microns. The resulting thick suspension may be applied directly, but preferably after being extended with oils or emulsified in water.

EXAMPLE 20

Wettable Powder

    ______________________________________                                         N--[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1,3-                                                       20%                                                dihydro-6-methyl-3-oxofuro[3,4-c]pyridine-4-                                   sulfonamide                                                                    sodium alkylnaphthalenesulfonate                                                                           4%                                                 sodium ligninsulfonate      4%                                                 low viscosity methyl cellulose                                                                             3%                                                 attapulgite                 69%                                                ______________________________________                                    

The ingredients are thoroughly blended. After grinding in a hammer-mill to produce particles essentially all below 100 microns, the material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) and packaged.

Utility

The compounds of the present invention are expected to be active herbicides. They should have utility for broad-spectrum pre- and/or post-emergence weed control in areas where complete control of all vegetation is desired, such as around fuel storage tanks, ammunition depots, industrial storage areas, oil-well sites, drive-in theaters, around billboards, highway and railroad structures. By properly selecting rate, time and method of application, one may use the compounds of this invention to modify plant growth beneficially, or to selectively control weeds in crops such as wheat and barley.

The rates of application for the compounds of the invention will be determined by a number of factors, including their use as plant growth modifiers or as herbicides, the crop species involved, the types of weeds to be controlled, weather and climate, formulations selected, mode of application, amount of foliage present, etc. In general terms, the subject compounds should be applied at levels of around 0.01 to 10 kg/ha, the lower rates being suggested for use on lighter soils and/or those having a low organic matter content, for plant growth modification or for situations where only short-term persistence is required.

The compounds of the invention may be used in combination with any other commercial herbicide examples of which are those of the triazine, triazole, uracil, urea, amide, diphenylether, carbamate and bipyridylium types.

Test A

Seeds of crabgrass (Digitaria spp.), barnyardgrass (Echinochloa crusgalli), wild oats (Avena fatua), cheatgrass (Bromus secalinus), giant foxtail (Setaria faberii), velvetleaf (Abutilon theophrasti), morningglory (Ipomoea sp.), cocklebur (Xanthium pensylvanicum), sorghum, corn, soybean, sugarbeet, cotton, rice, wheat, barley and purple nutsedge (Cyperus rotundus) tubers were planted and treated preemergence with the test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species were treated with a soil/foliage application. At the time of treatment, the plants ranged in height from 2 to 18 cm. Treated plants and controls were maintained in a greenhouse for sixteen days, after which all species were compared to controls and visually rated for response to treatment. The ratings, summarized in Table A, are based on a numerical scale extending from 0=no injury, to 10=complete kill. The accompanying descriptive symbols have the following meanings:

C=chlorosis/necrosis;

B=burn;

D=defoliation;

E=emergence inhibition;

G=growth retardation;

H=formative effect;

U=unusual pigmentation;

X=axillary stimulation;

S=albinism; and

6Y=abscised buds or flowers.

Compounds

    ______________________________________                                         Compound      X         Y          Z                                           ______________________________________                                          ##STR83##                                                                     1             OCH.sub.3 OCH.sub.3  CH                                          2             CH.sub.3  CH.sub.3   CH                                          3             CH.sub.3  OCH.sub.3  CH                                          4             Cl        OCH.sub.3  CH                                          5             CH.sub.3  OCH.sub.3  N                                           6             OCH.sub.3 OCH.sub.3  N                                            ##STR84##                                                                     7             OCH.sub.3 OCH.sub.3  CH                                          8             CH.sub.3  CH.sub.3   CH                                          9             Cl        OCH.sub.3  CH                                          10            CH.sub.3  OCH.sub.3  N                                           11            OCH.sub.3 OCH.sub.3  N                                           Compound 12                                                                             ##STR85##                                                             ______________________________________                                    

                                      TABLE A                                      __________________________________________________________________________             Compound 1                                                                             Cmpd. 2                                                                             Compound 3                                                                             Cmpd. 4                                                                             Cmpd. 5                                                                             Cmpd. 6                                 Rate kg/ha                                                                             0.05                                                                               0.01                                                                               0.05 0.05                                                                               0.01                                                                               0.05 0.05 0.05                                    __________________________________________________________________________     POSTEMERGENCE                                                                  Morningglory                                                                           10C 10C 3C,8G                                                                               10C 9C  4C,9G                                                                               10C  5C,9G                                   Cocklebur                                                                              10C 10C 3C,9H                                                                               10C 9C  9H   4C,9H                                                                               4C,8H                                   Velvetleaf                                                                             10C 10C 10C  10C 10C 9C   8H   3C,8H                                   Nutsedge                                                                               3C,8G                                                                              3C,7G                                                                              3C,9G                                                                               4C,9G                                                                              2C,8G                                                                              5G   0    3G                                      Crabgrass                                                                              3C,5G                                                                              2G  2G   6G  3G  0    0    0                                       Giant Foxtail                                                                          9C  2C,7G                                                                              0    2C,7G                                                                              1H  0    0    0                                       Barnyardgrass                                                                          9H  3C,7H                                                                              9H   9H  4H  3H   3H   2C,5H                                   Cheatgrass                                                                             4C,9G                                                                              6G  2G   2C,9G                                                                              4G  0    0    0                                       Wild Oats                                                                              2C,5G                                                                              0   0    2C,3G                                                                              0   0    0    0                                       Wheat   3G  0   0    5G  2G  2G   0    0                                       Corn    5C,9G                                                                              4C,9G                                                                              3C,9H                                                                               3C,9G                                                                              2C,9G                                                                              7G   2C,5H                                                                               0                                       Barley  2G  0   0    3G  0   0    0    0                                       Soybean 9C  9C  4C,9G                                                                               9C  5C,9G                                                                              7H   7H   2C,8G                                   Rice    9C  3C,7G                                                                              4C,9G                                                                               5C,9G                                                                              8G  7G   2G   3G                                      Sorghum 9G  3C,8G                                                                              4C,9G                                                                               4C,9G                                                                              2C,7G                                                                              4C,9G                                                                               2C,8H                                                                               3G                                      Sugar beet                                                                             10C 10C 9C   10C 9C  9C   9C   2C,8G                                   Cotton  10C 10C 4C,9G                                                                               10C 5C,9G                                                                              9C   9G   8G                                      PREEMERGENCE                                                                   Morningglory                                                                           5G  4G  5H   6G  3G  2G   3G   7G                                      Cocklebur                                                                              8G  8H  --   9H  9H  0    0    3H                                      Velvetleaf                                                                             8G  9G  9G   9G  4C,9G                                                                              0    4G   5H                                      Nutsedge                                                                               3G  0   5G   8G  0   0    0    0                                       Crabgrass                                                                              2G  0   0    0   0   0    0    0                                       Giant Foxtail                                                                          3G  0   2C   2C,3H                                                                              2G  0    0    0                                       Barnyardgrass                                                                          3G  1C  2C,3G                                                                               3C,7G                                                                              3G  0    0    0                                       Cheatgrass                                                                             7G  0   0    6G  4G  0    0    0                                       Wild Oats                                                                              0   0   0    2G  0   0    0    0                                       Wheat   3G  0   0    0   0   0    0    0                                       Corn    9H  7G  2C,6G                                                                               9H  7G  0    3G   3G                                      Barley  4G  0   0    0   0   0    0    0                                       Soybean 8H  7G  4H   9H  4H  0    1H   3H                                      Rice    9H  6H  8H   9H  10E 0    0    0                                       Sorghum 2C,8H                                                                              6G  3C,9H                                                                               2C,6G                                                                              2C,8G                                                                              0    0    0                                       Sugar beet                                                                             3C,8G                                                                              8G  7G   9G  7G  5G   3H   0                                       Cotton  9G  8G  4G   9G  8G  7G   3G   7G                                      __________________________________________________________________________             Compound 7                                                                             Cmpd. 8                                                                             Cmpd. 9                                                                             Cmpd. 10                                                                            Cmpd. 11                                                                            Compound 12                                Rate kg/ha                                                                             0.05                                                                               0.01                                                                               0.05 0.05 0.05 0.05 0.05                                                                               0.01                                   __________________________________________________________________________     POSTEMERGENCE                                                                  Morningglory                                                                           4C,9H                                                                              2C,6G                                                                              0    2C,4G                                                                               1H   2C,4G                                                                               0   0                                      Cocklebur                                                                              10C 8H  1H   6G   2G   4G   3G  0                                      Velvetleaf                                                                             5C,9G                                                                              8G  3G   0    2G   2G   2G  0                                      Nutsedge                                                                               9G  2C,8G                                                                              0    3G   0    0    0   0                                      Crabgrass                                                                              4G  0   0    0    0    0    2C,3G                                                                              0                                      Giant Foxtail                                                                          3G  0   0    0    0    0    3C,6G                                                                              3G                                     Barnyardgrass                                                                          9H  2C,7H                                                                              0    0    0    0    0   0                                      Cheatgrass                                                                             4G  0   0    0    0    0    2G  0                                      Wild Oats                                                                              0   0   0    0    0    0    3C,8G                                                                              2G                                     Wheat   2G  0   0    0    0    0    2C,5G                                                                              0                                      Corn    9H  2C,5H                                                                              2H   2C,5H                                                                               1C,5H                                                                               3H   3C,8H                                                                              5H                                     Barley  0   0   0    0    0    0    2C,4G                                                                              2G                                     Soybean 4C,9G                                                                              7H  0    2H   2H   2H   0   0                                      Rice    2C,8G                                                                              4G  2G   4G   2G   0    4C,8G                                                                              2G                                     Sorghum 7G  0   0    2G   0    2G   3C,6G                                                                              2G                                     Sugar beet                                                                             10C 4C,9G                                                                              1C   3G   2H   2C,5G                                                                               3H  0                                      Cotton  4C,9G                                                                              5G  2G   0    2G   4G   0   0                                      PREEMERGENCE                                                                   Morningglory                                                                           4G  3H  0    0    0    0    0   0                                      Cocklebur                                                                              8H  7H  0    0    --   0    0   0                                      Velvetleaf                                                                             7H  5G  0    0    0    0    0   0                                      Nutsedge                                                                               5G  0   0    0    0    0    0   0                                      Crabgrass                                                                              0   0   0    0    0    0    0   0                                      Giant Foxtail                                                                          0   0   0    0    0    0    0   0                                      Barnyardgrass                                                                          8H  0   0    0    0    0    0   0                                      Cheatgrass                                                                             0   0   0    0    0    0    0   0                                      Wild Oats                                                                              0   0   0    0    0    0    0   0                                      Wheat   0   0   0    0    0    0    0   0                                      Corn    4G  4G  0    0    0    2G   0   0                                      Barley  0   0   0    0    0    0    0   0                                      Soybean 3G  0   0    0    0    0    0   0                                      Rice    4G  0   0    0    0    0    0   0                                      Sorghum 3G  4G  0    0    0    0    0   0                                      Sugar beet                                                                             7G  4G  0    0    0    0    8G  5G                                     Cotton  7G  1H  0    0    0    0    0   0                                      __________________________________________________________________________ 

What is claimed is:
 1. A compound of the formula ##STR86## wherein J is: ##STR87## q is 0 or 1; Q is O, S or NR₄ ;Q₁ is O, S, SO, SO₂, NH or NCH₃ ; Q₂ is O, S, NH, NCH₃, CH₂ or CHCH₃ ; Q₃ is O, S, NH, NCH₃ or CH₂ ; R₄ is H or C₁ -C₄ alkyl; R₅ is H or CH₃ ; R₇ is H or C₁ -C₃ alkyl; R₁₇ is H or C₁ -C₄ alkyl; R₁₈ is H or CH₃ ; R₁₉ is H, F, Cl or C₁ -C₄ alkyl; R₂₀ is H, F, Cl or CH₃ ; R₂₁ is H, C₁ -C₃ alkyl, C₁ -C₃ alkoxy, F or Cl; R₂₂ is H, CH₃, C₁ -C₃ alkoxy, F, Cl or OH; or R₂₁ and R₂₂ can be taken together to form --OCH₂ CH₂ O-- or --OCH₂ CH₂ CH₂ O--; R₂₃ is H, C₁ -C₃ alkyl, C₁ -C₃ alkoxy, Cl, Br or F; W is O or S; R is H or CH₃ ; n is 0 or 1; R₁ is H, CH₃, OCH₃ or Cl; R₂ is H, C₁ -C₃ alkyl, Cl, Br, F, C₁ -C₃ alkoxy, C₁ -C₃ alkylthio, CF₃, CH₂ OCH₃, CH₂ SCH₃ or CH₂ CN; R₃ is H, C₁ -C₃ alkyl, halogen, C₁ -C₃ alkoxy, C₁ -C₃ alkylthio, C₁ -C₂ alkylsulfonyl, C₁ -C₂ alkylcarbonyl, C₁ -C₂ alkoxycarbonyl, C₃ -C₄ alkenyl, NO₂, NH₂, C₁ -C₂ alkyl amino, di(C₁ -C₂)-alkylamino, C₁ -C₂ alkylsulfamoyl, di(C₁ -C₂)-alkylsulfamoyl, (C₁ -C₂ alkyl)aminocarbonyl, di(C₁ -C₂ alkyl)aminocarbonyl or C₃ -C₄ alkynyl; R₆ is H, R₈ ', SR₈ ', SO₂ R₈, OR₈ ', C(O)R₈, CO₂ R₈ ', (CO)₂ OR₈, (CO)₂ R₈ ', C(O)NR₉ R₁₀, C(O)NRA, C(S)SR₈ ', NH₂, NR₉ R₁₀, OH, CN, P(O)R₁₁ R₁₂, P(S)R₁₁ R₁₂ or Si(CH₃)₂ R₁₃ ; R₈ is C₁ -C₁₀ alkyl, C₃ -C₁₀ alkoxyalkoxyalkyl, C₂ -C₁₀ alkenyl, C₃ -C₁₀ epoxyalkyl, C₂ -C₁₀ alkynyl, C₃ -C₆ cycloalkyl, C₄ -C₇ cycloalkylalkyl or phenyl optionally substituted with R₁₄ when R₈ is C₃ -C₆ cycloalkyl or C₄ -C₇ cycloalkylalkyl, it may optionally be substituted by C₁ -C₄ alkyl, 1 to 3 atoms of Cl or F or 1 Br; when R₈ is C₁ -C₁₀ alkyl, C₂ -C₁₀ alkenyl or C₂ -C₁₀ alkynyl, it may optionally be substituted by one or more halogens and/or by (R₁₅)_(r) provided that when r is 2, the values of R₁₅ may be identical or different; R₈ ' is C₁ -C₁₀ alkyl, C₃ -C₁₀ alkoxyalkoxyalkyl, C₃ -C₁₀ alkenyl, C₃ -C₁₀ epoxyalkyl, C₃ -C₁₀ alkynyl, C₃ -C₆ cycloalkyl, C₄ -C₇ cycloalkylalkyl or phenyl optionally substituted with R₁₄ ; when R₈ ' is C₃ -C₆ cycloalkyl or C₄ -C₇ cycloalkylalkyl, it may optionally be substituted by C₁ -C₄ alkyl. 1 to 3 atoms of Cl or F or 1 Br; when R₈ ' is C₁ -C₁₀ alkyl, C₃ -C₁₀ alkenyl or C₃ -C₁₀ alkynyl, it may optionally be substituted by one or more halogens and/or by (R₁₅)_(r) provided that when r is 2, the values of R₁₅ may be identical or different; r is 0, 1 or 2; R₉ is H or C₁ -C₄ alkyl; R₁₀ is H, C₁ -C₁₀ alkyl, C₁ -C₁₀ haloalkyl, C₃ -C₁₀ alkenyl, C₃ -C₁₀ alkynyl, C₃ -C₆ cycloalkyl or phenyl substituted with R₁₄ ; R₁₀ ' is C₁ -C₁₀ alkyl, C₁ -C₁₀ haloalkyl, C₃ -C₁₀ alkenyl, C₃ -C₁₀ alkynyl, C₃ -C₆ cycloalkyl or phenyl substituted with R₁₄ ; R₁₁ and R₁₂ are independently C₁ -C₄ alkyl, C₁ -C₄ alkoxy or C₁ -C₄ alkylthio; R₁₃ is C₁ -C₁₀ alkyl, benzyl or phenyl optionally substituted with R₁₄ ; R₁₄ is H, F, Cl, Br, CH₃, OCH₃, NO₂, CN, SCH₃, SO₂ CH₃ or CF₃ ; R₁₅ is OR₁₀, OC(O)R₁₀, OC(O)NR₉ R₁₀, OSO₂ R₁₀ ', OP(O)R₁₁ R₁₂, OSi(CH₃)₂ R₁₃, SR₁₀ ', SOR₁₀ ', SO₂ R₁₀ ', SCN, CN, SP(O)R₁₁ R₁₂, SP(S)R₁₁ R₁₂, P(O)R₁₁ R₁₂, P(S)R₁₁ R₁₂, NR₉ R₁₀, N+R₉ R₁₀ R₁₃, NR₉ C(O)R₁₀, NR₉ C(O)OR₁₀ ', NR₉ C(O)NR₉ R₁₀, NR₉ SO₂ R₁₀ ', NR₉ P(O)R₁₁ R₁₂, NR₉ P(S)R₁₁ R₁₂, NO₂, C(O)R₁₀, C(O)OR₁₀, C(O)NR₉ R₁₀, C(R₁₀)═NOR₁₂, naphthyl, phenyl optionally substituted with R₁₄ and/or R₁₆, ##STR88## R₁₆ is H, F, Cl, Br, ##STR89## X is H, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, C₁ -C₄ haloalkyl, C₁ -C₄ haloalkylthio, C₁ -C₄ alkylthio, halogen, C₂ -C₅ alkoxyalkoxy, amino, C₁ -C₃ alkylamino or di(C₁ -C₃ alkyl)amino; Y is H, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, C₁ -C₄ haloalkylthio, C₁ -C₄ alkylthio, C₂ -C₅ alkoxyalkyl, C₂ -C₅ alkoxyalkoxy, amino, C₁ -C₃ alkylamino, di(C₁ -C₃ alkyl)amino, C₃ C₄ alkenyloxy, C₃ -C₄ alkynyloxy, C₂ -C₅ alkylsulfinylalkyl, C₁ -C₄ haloalkyl, C₂ -C₅ alkylsulfonylalkyl, C₃ -C₅ cycloalkyl, C₂ -C₄ alkynyl, C₂ -C₅ alkylthioalkyl, ##STR90## or N(OCH₃)CH₃ ; W₁ and W₂ are independently O or S; m is 2 or 3; R_(a) is H or CH₃ ; R_(b) is C₁ -C₂ alkyl; R_(c) is C₁ -C₂ alkyl; Z is CH, CCH₃, CC₂ H₅, CCl or CBr; and their agriculturally suitable salts; provided that:(a) when W is S, then R is H, Z is CH and Y is CH₃, OCH₃, OC₂ H₅, CH₂ OCH₃, C₂ H₅, CF₃, SCH₃, OCH₂ CH═CH₂, OCH₂ C.tbd.CH, OCH₂ CH₂ OCH₃, CH(OCH₃)₂ or ##STR91## (b) when X is Cl, Br, F or I, then Z is CH and Y is OCH₃, OC₂ H₅, NH₂, NHCH₃, N(CH)₂, OCF₂ H; (c) when X or Y is C₁ haloalkoxy, then Z is CH; (d) when J is J₁, J₃, J₅, J₇, J₉, J₁₁, J₁₃, J₁₅, J₁₇, J₁₉, J₂₁, J₂₃, J₂₆ or J₂₈, then either R₁ or R₂ is H; (e) when the total number of carbon atoms in X and Y is greater than 4, then the total number of carbon atoms in J is less than or equal to 15; (f) the total number of carbon atoms in R₆ is less than or equal to 12; and (g) when R₁₅ and the bridging sulfonamide nitrogen of J₃, J₄, J₁₁ or J₁₂ is attached to the same carbon then R₁₅ is other than OH, SH, OC(O)R₁₀, OC(O)NR₉ R₁₀, OSO₂ R'₁₀, OP(O)R₁₁, R₁₂, OS:(CH₃)₂ R₁₃, SP(O)R₁₁ R₁₂, SP(S)R₁₁ R₁₂, NR₉ R₁₀ or N+R₉ R₁₀ R₁₃ ; (h) the total number of carbon atoms in R₁₉ and R₂₀ is less than or equal to 4; (i) the total number of carbon atoms in R₄ and R₅ is less than or equal to 4; (j) when R₂₁ is C₁ -C₃ alkoxy, then R₂₂ is H, CH₃ or C₁ -C₃ alkoxy; and (k) when R₂₂ is OH, then R₂₁ is H or C₁ -C₃ alkyl, and when R₂₂ is C₁ -C₃ alkoxy, then R₂₁ is H, C₁ -C₃ alkyl or C₁ -C₃ alkoxy.
 2. Compounds of claim 1 where J is ##STR92## q is 0 or 1; Q is O, S, or NR₄ ;Q₁ is O, S, SO, SO₂, NH or NCH₃ ; Q₂ is O, S, NH, NCH₃, CH₂ or CHCH₃ ; Q₃ is O, S, NH, NCH₃ or CH₂ ; R₄ is H or C₁ -C₄ alkyl; R₅ is H or CH₃ ; R₇ is H or C₁ -C₃ alkyl; R₁₇ is H or C₁ -C₄ alkyl; R₁₈ is H or CH₃ ; R₁₉ is H, F, Cl or C₁ -C₄ alkyl; R₂₀ is H, F, Cl or CH₃ ; R₂₁ is H, C₁ -C₃ alkyl, C₁ -C₃ alkoxy, F or Cl; R₂₂ is H, CH₃, C₁ -C₃ alkoxy, F, Cl or OH; or R₂₁ and R₂₂ can be taken together to form --OCH₂ CH₂ O-- or --OCH₂ CH₂ CH₂ O--; R₂₃ is H, C₁ -C₃ alkyl, C₁ -C₃ alkoxy, Cl, Br or F; provided that (a) the total number of carbon atoms in R₁₉ and R₂₀ is less than or equal to 4; (b) the total number of carbon atoms in R₄ and R₅ is less than or equal to 4; (c) when R₂₁ is C₁ -C₃ alkoxy, then R₂₂ is H, CH₃ or C₁ -C₃ alkoxy; and (d) when R₂₂ is OH, then R₂₁ is H or C₁ -C₃ alkyl, and when R₂₂ is C₁ -C₃ alkoxy, then R₂₁ is H, C₁ -C₃ alkyl or C₁ -C₃ alkoxy.
 3. Compounds of claim 2 wheren is 0; W is O; R is H; X is CH₃, OCH₃, OC₂ H₅, Cl, Br, F, I, OCF₂ H, CH₂ F, CF₃, OCH₂ CH₂ F, OCH₂ CHF₂, OCH₂ CF₃, CH₂ Cl or CH₂ Br; Y is H, CH₃, OCH₃, OC₂ H₅, CH₂ OCH₃, NHCH₃, N(OCH₃)CH₃, N(CH₃)₂, CH₂ CH₃, CF₃, SCH₃, OCH₂ CH═CH₂, OCH₂ C.tbd.CH, CH₂ OCH₂ CH₃, OCH₂ CH₂ OCH₃, CH₂ SCH₃, CH₂ SCH₂ CH₃, ##STR93## OCF₂ H, SCF₂ H, CH.tbd.CH or C.tbd.CCH₃ ; and Z is CH.
 4. Compounds of claim 3 whereR₂ is H, CH₃, OCH₃, Cl or Br; R₆ is H, R₈ ', C(O)R₈ or CO₂ R₈ '; R₈ and R₈ ' are C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, C₃ -C₆ alkneyl, C₃ -C₆ haloalkenyl, C₃ -C₆ alkynyl, C₃ -C₆ epoxyalkyl or C₁ -C₄ alkyl substituted with C₁ -C₂ alkoxy, C₁ -C₂ alkylthio, C₁ -C₂ alkylsulfinyl, C₁ -C₂ alkylsulfonyl, CO₂ (C₁ -C₂ alkyl), C(O)C₁ -C₂ alkyl, CN or OH; R₁₉ is H or C₁ -C₃ alkyl; R₂₀ is H or CH₃ ; R₂₁ is H, C₁ -C₃ alkyl or C₁ -C₂ alkoxy; R₂₂ is H, CH₃, C₁ -C₂ alkoxy or OH; or R₂₁ and R₂₂ may be taken together to form --OCH₂ CH₂ O-- or --OCH₂ CH₂ CH₂ O--; and R₂₃ is H, CH₃, Cl, Br or OCH₃.
 5. Compounds of claim 4 whereR₈ and R₈ ' are C₁ -C₆ alkyl, C₁ -C₄ haloalkyl, C₃ -C₄ alkenyl, C₃ -C₄ haloalkenyl, C₃ -C₄ alkynyl, CO₂ (C₁ -C₂ alkyl), C(O)C₁ -C₂ alkyl or C₁ -C₃ alkyl substituted with C₁ -C₂ alkoxy, C₁ -C₂ alkylthio, C₁ -C₂ alkylsulfonyl or CN.
 6. Compounds of claim 5 whereX is CH₃, OCH₃, OC₂ H₅, Cl, OCF₂ H or OCH₂ CF₃ ; and Y is CH₃, OCH₃, C₂ H₅, CH₂ OCH₃, NHCH₃ or CH(OCH₃)₂.
 7. Compounds of claim 6 where J is J₁.
 8. Compounds of claim 6 where J is J₃.
 9. Compounds of claim 6 where J is J₅.
 10. Compounds of claim 6 where J is J₇.
 11. Compounds of claim 6 where J is J₉.
 12. Compounds of claim 6 where J is J₁₁.
 13. Compounds of claim 6 where J is J₁₃.
 14. Compounds of claim 6 where J is J₁₅.
 15. Compounds of claim 6 where J is J₁₇.
 16. Compounds of claim 6 where J is J₁₉.
 17. Compounds of claim 6 where J is J₂₁.
 18. Compounds of claim 6 where J is J₂₃.
 19. Compounds of claim 6 where J is J₂₆.
 20. Compounds of claim 6 where J is J₂₈.
 21. Compounds of claim 1 where J is ##STR94## q is 0 or 1; Q is O, S, or NR₄ ;Q₁ is O, S, SO, SO₂, NH or NCH₃ ; Q₂ is O, S, NH, NCH₃, CH₂ or CHCH₃ ; Q₃ is O, S, NH, NCH₃ or CH₂ ; R₄ is H or C₁ -C₄ alkyl; R₅ is H or CH₃ ; R₇ is H or C₁ -C₃ alkyl; R₁₇ is H or C₁ -C₄ alkyl; R₁₈ is H or CH₃ ; R₁₉ is H, F, Cl or C₁ -C₄ alkyl; R₂₀ is H, F, Cl or CH₃ ; R₂₁ is H, C₁ -C₃ alkyl, C₁ -C₃ alkoxy, F or Cl; R₂₂ is H, CH₃, C₁ -C₃ alkoxy, F, Cl or OH; or R₂₁ and R₂₂ can be taken together to form --OCH₂ CH₂ O-- or --OCH₂ CH₂ CH₂ O--; R₂₃ is H, C₁ -C₃ alkyl, C₁ -C₃ alkoxy, Cl, Br or F; provided that (a) the total number of carbon atoms in R₁₉ and R₂₀ is less than or equal to 4; (b) the total number of carbon atoms in R₄ and R₅ is less than or equal to 4; (c) when R₂₁ is C₁ -C₃ alkoxy, then R₂₂ is H, CH₃ or C₁ -C₃ alkoxy; and (d) when R₂₂ is OH, then R₂₁ is H or C₁ -C₃ alkyl, and when R₂₂ is C₁ -C₃ alkoxy, then R₂₁ is H, C₁ -C₃ alkyl or C₁ -C₃ alkoxy.
 22. Compounds of claim 21 wheren is 0; W is O; R is H; X is CH₃, OCH₃, OC₂ H₅, Cl, Br, F, I, OCF₂ H, CH₂ F, CF₃, OCH₂ CH₂ F, OCH₂ CHF₂, OCH₂ CF₃, CH₂ Cl or CH₂ Br; Y is H, CH₃, OCH₃, OC₂ H₅, CH₂ OCH₃, NHCH₃, N(OCH₃)CH₃, N(CH₃)₂, CH₂ CH₃, CF₃, SCH₃, OCH₂ CH═CH₂, OCH₂ C.tbd.CH, CH₂ OCH₂ CH₃, OCH₂ CH₂ OCH₃, CH₂ SCH₃, CH₂ SCH₂ CH₃, ##STR95## OCF₂ H, SCF₂ H, CH.tbd.CH or C.tbd.CCH₃ ; and Z is CH.
 23. Compounds of claim 22 whereR₂ is H, CH₃, OCH₃, Cl or Br; R₃ is CH₃, CH₂ CH₃, F, Cl, Br, OCH₃, OCH₂ CH₃, SCH₃ SCH₂ CH₃, SO₂ CH₃, SO₂ CH₂ CH₃, SO₂ N(CH₃)₂, C(O)NHCH₃ or C(O)N(CH₃)₂ ; R₆ is H, R₈ ', C(O)R₈ or CO₂ R₈ '; R₈ and R₈ ' are C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, C₃ -C₆ alkenyl, C₃ -C₆ haloalkenyl, C₃ -C₆ alkynyl, C₃ -C₆ epoxyalkyl or C₁ -C₄ alkyl substituted with C₁ -C₂ alkoxy, C₁ -C₂ alkylthio, C₁ -C₂ alkylsulfinyl, C₁ -C₂ alkylsulfonyl, CO₂ (C₁ -C₂ alkyl), C(O)C₁ -C₂ alkyl, CN or OH; R₁₉ is H or C₁ -C₃ alkyl; R₂₀ is H or CH₃ ; R₂₁ is H, C₁ -C₃ alkyl or C₁ -C₂ alkoxy; R₂₂ is H, CH₃, C₁ -C₂ alkoxy or OH; or R₂₁ and R₂₂ may be taken together to form --OCH₂ CH₂ O-- or --OCH₂ CH₂ CH₂ O--; and R₂₃ is H, CH₃, Cl, Br or OCH₃.
 24. Compounds of claim 23 whereR₈ and R₈ ' are C₁ -C₆ alkyl, C₁ -C₄ haloalkyl, C₃ -C₄ alkenyl, C₃ -C₄ haloalkenyl, C₃ -C₄ alkynyl, CO₂ (C₁ -C₂ alkyl), C(O)C₁ -C₂ alkyl or C₁ -C₃ alkyl substituted with C₁ -C₂ alkoxy, C₁ -C₂ alkylthio, C₁ -C₂ alkylsulfonyl or CN.
 25. Compounds of claim 24 whereX is CH₃, OCH₃, OC₂ H₅, Cl, OCF₂ H or OCH₂ CF₃ ; and Y is CH₃, OCH₃, C₂ H₅, CH₂ OCH₃, NHCH₃ or CH(OCH₃)₂.
 26. Compounds of claim 25 where J is J₂.
 27. Compounds of claim 25 where J is J₄.
 28. Compounds of claim 25 where J is J₆.
 29. Compounds of claim 25 where J is J₈.
 30. Compounds of claim 25 where J is J₁₀.
 31. Compounds of claim 25 where J is J₁₂.
 32. Compounds of claim 25 where J is J₁₄.
 33. Compounds of claim 25 where J is J₁₆.
 34. Compounds of claim 25 where J is J₁₈.
 35. Compounds of claim 25 where J is J₂₀.
 36. Compounds of claim 25 where J is J₂₂.
 37. Compounds of claim 25 where J is J₂₄.
 38. Compounds of claim 25 where J is J₂₇.
 39. Compounds of claim 25 where J is J₂₉.
 40. Compounds of claim 1 where J is ##STR96## and R₂₃ is H, C₁ -C₃ alkyl, C₁ -C₃ alkoxy, Cl, Br or F.
 41. Compounds of claim 40 whereW is O; R is H; X is CH₃, OCH₃, OC₂ H₅, Cl, Br, F, I, OCF₂ H, CH₂ F, CF₃, OCH₂ CH₂ F, OCH₂ CHF₂, OCH₂ CF₃, CH₂ Cl or CH₂ Br; Y is H, CH₃, OCH₃, OC₂ H₅, CH₂ OCH₃, NHCH₃, N(OCH₃)CH₃, N(CH₃)₂, CH₂ CH₃, CF₃, SCH₃, OCH₂ CH═CH₂, OCH₂ C.tbd.CH, CH₂ OCH₂ CH₃, OCH₂ CH₂ OCH₃, CH₂ SCH₃, CH₂ SCH₂ CH₃, ##STR97## OCF₂ H, SCF₂ H, CH.tbd.CH or C.tbd.CCH₃ ; and Z is CH.
 42. Compounds of claim 41 whereR₂ is H, CH₃, OCH₃, Cl or Br; R₃ is H, CH₃, CH₂ CH₃, F, Cl, Br, OCH₃, OCH₂ CH₃, SCH₃, SCH₂ CH₃, SO₂ CH₃, SO₂ CH₂ CH₃, SO₂ N(CH₃)₂, C(O)NHCH₃ or C(O)N(CH₃)₂ ; and R₂₃ is H, CH₃, Cl, Br or OCH₃.
 43. Compounds of claim 42 whereA is A-1; X is CH₃, OCH₃, OC₂ H₅, Cl, OCF₂ H or OCH₂ CF₃ ; and Y is CH₃, OCH₃, C₂ H₅, CH₂ OCH₃, NHCH₃ or CH(OCH₃)₂.
 44. The compound of claim 1 which is N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]thieno[2,3-C]pyridine-7-sulfonamide.
 45. The compound of claim 1 which is N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]thieno[2,3-C]pyridine-7-sulfonamide.
 46. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 1 and at least one of the following: surfactant, solid or liquid diluent.
 47. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 2 and at least one of the following: surfactant, solid or liquid diluent.
 48. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 21 and at least one of the following: surfactant, solid or liquid diluent.
 49. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 40 and at least one of the following: surfactant, solid or liquid diluent.
 50. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 44 and at least one of the following: surfactant, solid or liquid diluent.
 51. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 1. 52. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 2. 53. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 21. 54. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 40. 55. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 44. 